Richard Montgomery

Richard Montgomery is no nonsense real estate advice syndicated in over 300 newspapers around the nation. When preparing to buy or sell a home, you get the best advice, when you need it and at no cost to you: 

*An intelligent selection service to help you pick the right real estate
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the right answers during the process.
*An extensive “How To” library on important real estate subjects to
review while getting ready.

Readers gain a business advantage by engaging for unbiased real estate expertise, to save valuable time and leverage DearMonty s 25 years of experience selecting real estate agents.
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University of Wisconsin Green Bay (UWBG)


Respect for the individual

Affiliations, National Association of Realtors, Realtors Association of NE Wisconsin


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Displaying Results 1 - 100 (of 116) for All Content
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  • 13 “red Flags” that Affect Home Values
    A reader who had trouble selling their flawed home ask Monty what to watch out for on their next home. Monty lists 13 "red flags" to check out.
  • Five Important Tips When Considering Cooperative Housing
    A reader asks Monty for information and advice regarding the cooperative housing lifestyle. Monty shares some links and five tips when searching for co-op housing.
  • Timing Your Retirement Home Purchase
    A senior reader asks Monty for advice in obtaining a "bridge loan". Monty shares pointers but goes on to suggest they may not need one.
  • Get the Facts Before Deeding Your House to the Bank
    An 83 year-old reader asks Monty if she should deed her home to the bank. Monty says "Not so fast."
  • Senior Housing Options Offer Challenges
    A reader asks Monty for help in negotiating on a home purchase in a senior community. Monty offers up some observations and 6 tips for changing the playing field.
  • 9 Tactics Not Found on a Due Diligence List
    A reader contemplating purchasing a large apartment building asks Monty for some "outside the box" due diligence tactics. Monty shares a number of tactics not generally found on a due diligence checklist.
  • Full-service Real Estate Agents Versus FSBO Companies
    A reader selling their home asks Monty for a comparison between a FSBO real estate company and a traditional full service company. Monty shares his viewpoint in a service schedule.
  • Understanding the Real Estate “buyers Agent” Fee
    A reader asks Monty if a buyer pays a fee when buying real estate
  • 7 Tips for Discovering the Best Use for Property
    A reader asks Monty for help finding a buyer for a property they believe should be utilized as a group home. Monty shares 7 tips that will help them discover if they are on the right track.
  • Selling a Nice Home in a Distressed Neighborhood
    A reader trying to sell her home blames the neighbors for lack of a sale. Monty suggests there may be other causes to consider and ways to correct them.
  • Building a Real Estate Investment Team
    A reader contemplating their first real estate investment asks Monty how to build a team to help. Monty shares the major considerations to help decide.
  • Elderly Seller Avoids Remodeling
    An elderly home seller asks Monty for the pros and cons of remodeling when selling. She doesn't want the task. Monty shows her a marketing tactic to help her sell without fixing up.
  • The Benefits of Owning Small Apartment Buildings
    A reader with two buildings in their portfolio and getting ready for a third asks Monty if they should try to buy larger buildings. Monty suggests the reasons for continuing on with smaller properties.
  • Contractual Error Costly for Real Estate Agent
    A real estate agent asks Monty for help on fixing a contract error. Monty lays out a plan that repairs the contract problem and makes the seller and the buyer happy.
  • Passing Time Can Change Property Use
    A reader that develops apartments asks Monty the difference between developing for apartment sites and single family home sites. Monty lays out an overview of the major considerations in switching gears.
  • Utility Bill Increase Squeezes Tenants
    A reader asks Monty if a big increase in a utility bill is legal. Monty shares a plan to help the tenants understand the formulas that drive the increase.
  • Using the Same Agent when Downsizing Homes
    A reader asks Monty if it is wise to use the same agent selling the home in the purchase of a different home. Monty's answer is often it can be okay, but sometimes not.
  • Can a Real Estate Transaction Be Illegal?
    A reader asks Monty if a real estate agent can use a straw man to purchase a home. Monty shares examples of when it is legal and when it is not legal.
  • How to Raise Rents
    A new real estate investor is afraid to raise rent in a soft economy even though expenses are up. Monty shows them a way to make a good decision.
  • To Move or Not to Move - the House?
    A reader asks Monty if moving their home a few feet to create a new lot on their property is worth the expense. Monty shares information to help them decide.
  • Tips on Making Your First Real Estate Investment
    A reader considering making a real estate investment asks Monty for some tips. Monty delivers a number of practical tips to help get off to a good start.
  • Real Estate Rehab Gone Wild - the Options?
    A reader asks Monty for advice because they walked from from a rehab deal and the contractor/owner will not refund the down payment and material advances to the project.
  • Handling Real Estate Agent Rejection
    A reader in a very large city is pre-qualified with good jobs but no agent will work with them. Monty shares the reason and defeats the situation with a tactic.
  • Compare Building a New Home to Buying a Pre-owned Home
    A reader asks Monty for a comparison between building a new home and buying an existing home. Monty obliges with the economic theory and some buying advice.
  • Sleuthing a Real Estate Issue – Your Personal Reality Game
    A reader asks Monty for help with a problem that triggered a loan rejection. Monty suggests the reader dig in and suggests where to find some answers
  • Developer Track Record Important in Housing Projects
    A reader asks Monty advice on getting the parking space they were promised when they purchased their condo. Monty lays out advice on what they need to know before deciding on a plan.
  • Converting the Garage to Living Space
    A reader asks Monty if converting the garage into living space will devalue their home. Monty weighs in with a formula to help the homeowner determine the answer.
  • Water Management Issues Can Be Dicey with Neighbors
    A reader asks Monty what to do about a neighbor who has recently installed drain hoses that drain towards their backyard. Monty lays out a plan to help.
  • Occupancy at Closing is Risky for the Home Seller
    A reader contemplating an offer that wants the seller to vacate on the day of closing asks Monty if this is a good idea? Monty suggests not, unless the offer is cash with a good earnest money deposit.
  • A Senior Housing Dilemma
    A senior reader asks Monty for advice in making sense of all housing options and programs for seniors to consider as they age. Monty lays out a plan to simplify the information for their use.
  • Presto! Change a One Family Home into a Two Family Home
    A reader asks Monty if they should create a two family while remodeling their home. Monty shares some ideas to consider first and foremost when thinking of changing the use of real property.
  • A Perfect Storm - How to Create Poor Real Estate Decisions
    Sometimes it is difficult to see the important issues because some event or item distracts the participants from the main concern. These questions illustrate how easy it is to get off track.
  • A Home Seller's Checklist
    A reader asks Monty how to best deal with all the advice neighbors are sharing about placing their home on the market. Monty provides a checklist and a method to handle the neighbor's advice.
  • Who Should Own Rental Property?
    A reader asks Monty if a real estate agent should return a rental commission as the tenant only paid the first month. Monty's answer may surprise you.
  • Mortgage Loan Approvals Can Be Confusing
    Readers selling homes often ask Monty's advice about dealing with the buyers financing contingency. It is easy to make mistakes at this critical time in the real estate process.
  • Dealing with "condition Issues" when Selling Your Home
    A reader asks Monty if they have to disclose the fact the garage floods during a heavy rain on the seller disclosure report. Monty tells them "yes" and gives them a number of pointers on how to deal with it.
  • Considerations in Remodeling an Old Farmhouse
    A reader asks Monty for advice about buying and remodeling an old farmhouse. Monty shares information that will assist them in determining the best way to proceed.
  • First Person: Creating Your Own Job After Retirement
    Going back to work was the furthest thought from my mind in 2010. But as we all experience in life, certain events can change our plans in a heartbeat. This is my story.
  • A Smart Way to Choose Between Neighborhoods
    A reader having difficulty deciding which area to live in asks Monty if they should utilize different agents to look or stick with one agent. Monty has a number of suggestions that will lead them to the right answer.
  • How to Deal with a Dirt Basement Floor
    A reader asks Monty if value is created by pouring concrete on a dirt basement floor. Monty shares some pointers but asks many questions.
  • To Sue, or Not to Sue? a Prickly Decision
    A reader asks Monty of their chances recovering damages from a failed real estate closing. Monty cautions them "never get in a fight you are not sure of winning."
  • How to Protect Your Home Equity in a Divorce
    A reader asks Monty if it is legal to pay a commission to her soon-to-be ex-husband who is a real estate agent. Monty answers her question and suggests there are larger issues to focus upon.
  • How to Handle Occupancy After Closing a Home Sale
    A reader asks Monty about protecting himself financially from damage to the home he is buying. He has already signed a purchase agreement and agreed to let the seller stay for 30 days. Monty has some advice but it may be too late.
  • Home Inspections Go Wrong in More Ways Than One
    Two readers have issues; one with a home inspection the other with inspection contractual procedures. Monty shares his thoughts with both parties to bring relief.
  • How to Determine Which Items to Leave when Selling a Home
    A reader selling his deceased parents home asks Monty whether to leave or take several items from the home when selling it. Monty shares a checklist to use on each item to answer the question.
  • Overcoming a Real Estate Inspection Defect
    A reader asks Monty for guidance in negotiating an inspection defect against a seller who has backup offers on the home. Monty provides some good pointers in what could be a very difficult situation to negotiate.
  • The Best Place to Buy Real Estate
    A reader asks Monty to compare certain statistics between two cities to help them decide where to invest in real estate. Monty switches direction and offers a different answer that may surprise them.
  • "Madder Than a Wet Hen"
    A reader is angry about a clause that was agreed to in the listing that came to fruition and asks Monty if it is legal. Monty answers the question and shares the benefit of co-brokerage in real estate sales.
  • 5 Tips for Singles Buying First Home
    A single reader preparing to go out looking to buy their first home asks Monty who to take with her and for his advice to singles. Monty answers the question and shares 5 tips to help.
  • Are Your Hands Tied Trying to Close Your Real Estate Transaction?
    A reader asks Monty what they should do about their real estate situation. Their agent suggests they close on a 3 unit building when they learn 5 days before closing it is only legal for two units. Monty has a plan.
  • Refurbish or Remove an Old Swimming Pool?
    A reader asks Monty if they should invest in refurbishing the pool or demolishing it. Monty demonstrates how they can determine which is the best choice.
  • 6 Good Tips to Prepare for an Offer on Your Home
    A home seller who was just notified by their real estate agent an offer is coming in on their home ask Monty what they can do to prepare to react intelligently. Monty shares 6 good tips to simplify the process.
  • Selling Your Home? Be Certain to Check Out the Competition
    A reader asks Monty what market information will help them determine the initial list price when their home hits the market. Monty shares the key data points and suggests there are other uses for the data.
  • Real Estate Agent Puts Commission at Risk
    A reader questions their obligation to a real estate agent showing the reader's property to a customer without a listing. Monty shares the owners's options and adds a bit of extra counsel.
  • Buying a Home? Avoid Risking Your Earnest Money Deposit
    A reader asks Monty for ideas on recovering a lost $5000 earnest money deposit. Monty shares some ideas but cautions that it may be too late. Then points the buyer to some suggestions so it does not happen again.
  • 5 "Pick a Broker" Tips for New Real Estate Agents
    A reader considering studying for a real estate license with questions about which school and how real estate companies work asks Monty for advice. Monty answers the questions and adds some tips on how to figure out the best place to work.
  • Beware of Loan Modification Scams
    A reader questions Monty on the legitimacy of a loan modification business. Monty declines to rate a particular business but provides information and commentary on how to search for a loan modification.
  • Why the "Home Lookers List" is Hard to Obtain
    A reader asks Monty if it is proper to request a list of people who have viewed their home. Monty answers yes, but goes on to describe why it may be difficult for a real estate agent to comply.
  • The Best Method to Value Small Business Property
    A reader is planning on selling their business which includes real estate. They ask Monty to recommend an appraiser. Monty has a different idea as to how they should proceed.
  • Why Some Commercial Real Estate Ends Up like This?
    An enthusiastic reader asks Monty for advice about buying commercial real estate. Monty lays out a plan for both novices and more experienced participants to help them set a course to successful investing.
  • Selling Church Property Requires Expertise
    A reader is charged with selling off excess property for his church. He asks what to do next now that a price has been established. Monty answers his question and offers up more questions.
  • The Risk of Borrowing Money from Your Parents
    A reader fears they will be unable to repay a loan from her parents upon the sale of her home and asks Monty for advice. Monty lays out 4 steps that must be taken to provide the information needed to make the right decisions.
  • 5 Best Tips for Newbie Renting Roommates
    Friendships are often tested when 2 or more people decide to live together. Experience shows that by having a plan in place beforehand can mean the difference between a positive experience and an early parting of the ways.
  • Making Adjustments Indispensable when Valuating Property
    A reader questions an appraisal when discovering not one of the comparable sales included an indoor riding facility yet the subject property featured one. Monty agrees and shares information about making adjustments to sold comparables.
  • Todays 3 Choices to Find a Real Estate Agent
    A reader asks Monty for advice about how to find a real estate agent. Monty outlines the 3 choices real estate consumers have today and how the internet has created more of them.
  • 5 Best Home Buying Tips in a Sellers Market
    A reader is frustrated because they lose every time they offer to buy a home. Monty redirects them and gives them the 5 best tips for winning the home of their dreams.
  • Expertise Required Evaluating Investment Property
    A reader is questioning appraisal techniques while assisting family members shed real estate assets for retirement. Monty answers his questions but suggests additional research to make a final decision.
  • Get Facts Before Throwing in the Foreclosure Towel
    A reader with two homes is concerned the "underwater" home will cause him to also lose his personal residence in which he has equity. Monty gives him a path to follow.
  • 4 Smart Tips About Home Price Reductions
    A reader reacts to her real estate agent's suggestion that the price be reduced. Monty's shares 4 data point sources that will help in the decision.
  • Buying Commercial Property for Use as Personal Storage
    A reader buying commercial property for storage asks about the best way to finance and insure it. Monty provides some interesting information.
  • Calculating the Risk of Owning Two Homes
    Many real estate consumers want to move to a larger home, or a smaller home. Both of these homeowners face the ultimate real estate question, "Should I sell before I buy? or, Should I buy before I sell? Monty answers that question for a reader.
  • Evaluating an Unsolicited Offer Requires Work
    When some people receive a proposal unexpectedly, it is not uncommon for the recipient to focus on the proposal without stepping back and giving the situation a more global look. Not doing this can result in an unhappy ending.
  • Is Your Neighbor Committing Mortgage Fraud?
    Mortgage fraud is on the rise in the United States. Short sales are only one of the areas that abuse can occur. Monty's reader is asking what to do about it when you find out someone is involved. The answer is in this article.
  • Challenging Real Estate Tax Assessment for Non-delivery of Services
    A reader asks Monty if they can challenge their real estate tax bill because the city does not provide them with services like the rest of the city. Monty suggest not, but shares a path to determine probable success in advance.
  • "For Sale" Sign Installed Without Permission
    A reader discovers his neighbor placed a "For Sale" sign on his property without permission and wants to know what he can do about it. Monty's answer may surprise you.
  • Take Caution Buying an Old Manufactured Home
    A first time home buyer approved by FHA for a home loan is blocked because the manufactured home was pre-1976 and FHA will not finance it. Monty gave them options, and told them why FHA said no.
  • Pay Attention when Planning Concrete Driveways
    A reader asks Monty if he can sue the contractor 12 years after the improper installation of a concrete driveway. Monty confirms it is too late for that, but has different ideas about the cause.
  • Solving a Real Estate "Cold Case"
    A reader wonders if pursuing a real estate offer after an outstanding unpaid mortgage is discovered that causes the title company to decline insuring the property. Monty suggests a few ideas that may save the deal.
  • Making a Home Offer Right the First Time
    A reader writes to ask how much below the asking price is reasonable to bid. Monty shares the problem with making uncalculated offers and a better way to proceed.
  • A Land Contract is a Viable Home Finance Option
    A reader asks for information about a seller providing a private loan. Monty shares the answer to explain the land contract as a viable alternative to a mortgage if properly vetted.
  • 3 Tips to Master Evaluating a Home
    A first time home buyer discovers the many DearMonty articles and asks if there is one subject that encapsulates the home buying process. Monty points them to learning to understand how to value a home.
  • Tips to Make Finishing Your Basement Pay
    A reader with conflicting information asks which numbers are reliable in determining the extra value finishing the basement provides. Monty shares a number of considerations that suggest the only way to know is make a plan and price it out.
  • Tips on Evaluating Vacant Land
    A reader asks Monty what a parcel of land is worth. Monty informs them he cannot answer without walking the land, but offers the reader tips to understand in determining value.
  • The Mystery of the Defective Dryer Vent
    Home seller upset to learn home inspection reveals old dryer vent code violation. Monty shares strategy to uncloak the offender.
  • Home Seller Not Obligated to Buyer Offer
    Reader asks if their offer obligates the seller to negotiate with them first. Monty says "no", but explains how the process works and why it can be difficult.
  • 8 tips for seniors thinking of downsizing
    Downsizing for seniors sometimes has thorny considerations when making plans for the the golden years. Here are some simple tips that may come in handy.
  • Reaffirming a Mortgage After Bankruptcy
    The reader encounters one of the nuances in today's turbulent mortgage market trying to refinance. Monty suggests steps to take in determining if reaffirmation is the real problem.
  • Strategies in Choosing a General Contractor
    A businessman queries Monty about how to find a general contractor for a large remodeling project. Monty lays out a method to identify and hire a good one.
  • The Respectable Outcome for Homeowners in the Real Estate Meltdown
    A reader wants to know the respectable way out of their underwater mortgage. DearMonty runs them through all the options and writes about the attitudes to guide the decision.
  • The Downside to a Tough Home Negotiation
    A prospective home buyer is negotiating over repairs required in the home inspection and the seller stops talking. DearMonty shares some tips about how to prevent this from happening on the next offer.
  • A Remodel Can Create an Undesirable Floor Plan
    A bathroom has two entrances. The question is about trading the second entrance off the master bedroom for a bathtub. The concern of the reader is salability. Monty has the answer.
  • New Home Buyer Frustrated with Sewer Backups
    An attorney asks Monty for help in solving his clients problem. Monty suggests the problem may not be with the builder, but the owner of the sewer system.
  • Buying Homes with Prices This Low
    A reader asks Dear Monty how many homes to buy with prices this low. Dear Monty's no nonsense real estate advice turns the tables on the reader by suggesting they ask themselves some questions.
  • Five Renovation Tips in Run-down Neighborhoods
    Reader seeks advice for buying a fixer-upper in a run-down neighborhood. Dear Monty's no nonsense advice provides great direction.
  • Are Savings Possible Combining Adjoining Tax Parcels
    Monty's no nonsense answer to a readers question regarding reducing real estate taxes by consolidating adjoining lots by survey. Monty suggests a way to determine if it is feasible before any money is spent.
  • Participating in the Foreclosure Market
    Monty is asked to give real estate advice about how to search for homes in the foreclosure market. He describes the three types of foreclosure property and the four types of agents that sell them.
  • What to Expect from Your Agent as a Buyer
    A potential home buyer asks Monty's real estate advice to lay out a job description they can utilize to help them in the agent selection process. Monty's no nonsense answers lay it out clearly for them.
  • Homeowner Mulls Trading Part of Lot with Neighbor
    A reader asks Dear Monty for advice on trading land with their neighbor. They get no nonsense advice from Monty, but not what they were expecting.
  • Home Buyer's Offer Always Beaten
    Reader asks Monty what can be done to compete with other homebuyers that are paying cash for homes. The reader is questioning the feedback they are getting from their agent. Monty provides them some no nonsense real estate advice.
  • CEO Negotiates New Job Benefits
    The relocation package can make or break the successful new executive hire. Understanding the benefits many companies negotiate can make a difference. It is a competitive landscape and the playing field is constantly changing. Knowledge is power.
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