Lessons from the Landlady: How to Avoid My Mistakes and Be Successful in Real Estate

By Wendy Myers

Do you want to jump into real estate but are afraid of the day-to-day tasks? Do you yearn to own property but are not sure how to handle the rental process from beginning to end? Do you already own rental property but are tired of the hassles and headaches? Ask the landlady! She has the answers to all your questions about becoming a landlady or

• Language: English
• Publisher: Ask the Landlady
• Release date: Sep 15, 2023
• ISBN: 9798988607717

Book preview

Praise for Lessons from the Landlady:

How to Avoid My Mistakes and Be Successful in Real Estate

Lessons from the Landlady is a must-read book for anyone wanting to jump into the rental business as a side hustle or main gig. Most business owners don’t like to talk about their failures, but Wendy Myers honestly outlines all her mistakes so that readers can avoid them, ensuring that they make a high profit and stay out of trouble. 

—    William Bronchick, attorney and best-selling real estate author

Don't rent your property without first reading Lessons from the Landlady! This book will save you time and money by showing you how to avoid all the pitfalls that so many other landlords make. Wendy shares her journey in a fun, light-hearted way that provides education that is easy to absorb and able to put into action immediately.

—    Becky Nova, Founder of Lady Landlords, a community for women reaching financial freedom through real estate investing.

As a 40-year seasoned educator of tens of thousands of mom and pop landlords and bestselling author and senior editor of the national Mr. Landlord newsletter, I recommend Ask the Landlady as a must-read for anyone wanting to jump into real estate rentals or build on an existing portfolio of rental properties. In this book, Wendy provides an honest perspective of what it is really like to own rental properties and deal with all the entities, from banks and insurance companies to tenants and government agencies. She also provides practical, creative and proven land lording tips.

—    Jeffrey Taylor, C.P.L., [e-mail]

Providing housing for others can be a noble (and lucrative) career or side gig. However, it is best done in the intentional, professional manner described in Lessons from the Landlady. While there are many ways to invest in real estate, as entrepreneurial ventures go, there are few that reliably lead to wealth as well as direct real estate investing. 

—    James M. Dahle, MD, Founder of The White Coat Investor

As someone who embraces a FIRE (financial independence, retire early) philosophy, I applaud those who embark on real estate investment as part of their financial portfolio. Real estate is always on the top of the list for passive income options. Wendy started real estate as a side hustle and turned it into a full-time retirement option. Lessons from the Landlady reads like a handbook with real-life examples so that readers can duplicate her success.

—    Jorge Sanchez, MD, author and blogger at Physician on FIRE, a website created to inform and inspire with insightful writing from a physician who has attained financial independence and the ability to retire early.

Landlady Wendy Myers humorously draws from real life stories to teach how to leverage your existing skill set and experiences to jump start your real estate business. She is transparent from her own experiences, learning from mistakes, the joy of providing value and the reality of flexible schedules. Lessons from the Landlady is a mandatory addition to anyone breaking into the real estate world!

—    Dr. Jennifer Salisbury (Dr. Jen), former US Navy Nuclear Propulsion Engineer, dynamic educator and host of the podcast, My Life as a Landlord.

Published by Ask the Landlady

Marietta, Ohio

©2023 Ask the Landlady LLC

All rights reserved.

Library of Congress Control Number:

2023911415

The author and publisher have taken reasonable precautions in the preparation of this book and believe the facts presented in the book are accurate as of the publication date. However, neither the author nor the publisher assumes any responsibility for any errors or omissions. The author and publisher disclaim any liability resulting from the use or application of the information contained in this book and the information is not intended to serve as financial, legal or other business advice related to individual situations.

No part of this book may be reproduced, stored in a retrieval system, or transmitted by any means, electronic, mechanical, photocopying, recording or otherwise, without written permission from the copyright holder.

Dedication

To my fantastic, supportive family who will probably never read this book in its entirety. But if you made it this far — just know how much I love you all.

Prologue:

A Note about Terminology

There are several different terms given to those of us who invest in real estate and then rent property to commercial or residential tenants. Unlike other professions—nurse, lawyer, social worker, flight attendant—our profession has a myriad of different monikers. While what you choose to call yourself is your decision, I would like to provide some perspective and tell you why I chose landlady for myself.

It is a tired old tale; tenants love to complain about their landlords. We see it all the time in social media posts and in song lyrics. Bob Dylan sang: Dear landlord/Please don’t put a price on my soul in his 1967 folk song written about getting his rent lowered. And in the 1980s, Blood in the Saddle, a country punk band, sang: "I see the landlord coming gonna knock on my door /Better give me some money, boy, or you can't live here no more/Landlord, landlord, take it easy on me/Landlord, landlord, I don't have no money. And more recently, Nicki Minaj sang: And I am not paying my rent this month, I owe that." So basically, no one wants to give money to a landlord, and everyone likes to complain about rent.

A recent Twitter search showed a variety of memes about landlords, all invoking negative imagery. Several memes compared landlords to leeches or cockroaches. One popular meme had the title: Landlords be like and the landlord who is sitting there pondering the basic human need for shelter and then decides that the basic need is, indeed, a profit opportunity. @smoothposer on Instagram wrote: Gotta feel bad for landlords. Some of them are rich yes, but many are living from your paycheck to your next paycheck. On any given day, you have probably heard someone complain that the landlord won’t fix anything or keep up the property. Indeed, renters and landlords have always had a contentious and somewhat complicated relationship.

The term landlord goes back to Old English and has its roots in a medieval feudal system of lords renting tenancy of their lands to farmers. The term is literally equivalent to land + lord. According to the Online Etymology Dictionary, the roots of lord equate to master of a household, ruler, feudal lord, superior; husband. Of course, this is all heavy-handed terminology that is not relevant in modern times. Thus, new terminology has emerged.

Those of us who rent properties are often called property managers or leasing agents. On all official documents, I list my profession as property manager even though I’m not sure why the doctor’s office needs to know this when I’m just getting my cholesterol checked every year.

However, these more modern terms do not adequately define those of us who own and operate our own rental businesses. I’ve been among other property owners who title themselves real estate investors or Real estate business owners but these also do not fully define all we do on an ongoing, daily basis.

So, when I use landlady I’m taking into account all of these factors. I own my stuff and rent it out so landlord is applicable, except that I’m not male (and some may argue that I’m not a lady—but that’s not the point. My friends have always been too truthful, lol). The terms that use manager or agent make people think I’m an employee, and investor or owner is incomplete because I do take an active interest in the management of my own properties. So, for all these reasons, I use landlady. And I use it with pride because I’m also taking back the patriarchal terminology. Since I’m often at property events, banks, or closings, I’m among a lot of men in the room. And a lot of the crusty older landlords see me as a little lady who should let her husband take care of things. In fact, when I tried to start a landlord association in my small Ohio town, the men promptly tried to take it over and take credit for my work. (True story, they suck.) That is why I decided to write a book. The men in that room didn’t think I had anything worthwhile to say. In any case, they were all too busy posturing and talking over each other to stop and listen.

So, I choose to take a page from the book of our great American icon, Dolly Parton. Her entire career people have tried to make her the victim of sexual jokes and put her down as a dumb blonde. Dolly even wrote a song about it. If you ever saw her on the late show with Johnny Carson, you would notice that she made fun of herself and owned the terminology and jokes about her body. When pushed to make a statement on feminism, Dolly Parton said, I just really feel I can live my femininity and actually show that you can be a woman and you can still do whatever you want to do. I like that.

So unapologetically, I’m a landlady. I’m going to use that term throughout this book. However, you be you. Choose the term that you like best when you carve out this career. Because this path is not for the faint of heart. It takes hard work, perseverance and, most importantly, the ability to learn from mistakes. Over the course of several chapters, I will tell you about all my mistakes and how I pivoted these into learning opportunities and built a successful real estate business. So, if you have courage and want to go down this path—be a badass and call yourself whatever you want. Other people are going to call you all sorts of things. Here’s just a sampling of what I have been called: slumlord, bitch, Scrooge, greedy bastard, bloodsucker, dragon lady, and so on. So do yourself a favor upfront; pick a term you like and one you can wear with pride. Let that term define you and set you up for success.

Table of Contents

Prologue: A Note about Terminology

Chapter One: An Accidental Landlady

Chapter Two: Blissful Ignorance

Chapter Three: Setting Up Your Business

Chapter Four: Finding Properties to Buy

Chapter Five: Evaluating the Deal

Chapter Six: Procuring the Money to Pay for The Property

Chapter Seven: Negotiating a Price for A Property

Chapter Eight: Advertising the Property

Chapter Nine: Selecting the Tenant

Chapter Ten: Securing a Lease with the Tenant

Chapter Eleven: Taking Care of Insurance And Legal Issues

Chapter Twelve: Collecting Monthly Rent

Chapter Thirteen: Ongoing Maintenance

Chapter Fourteen: Troubleshooting

Chapter Fifteen: Improving Your Process

Glossary of Terms

Forms List

Chapter One

An Accidental Landlady

Mistake: I didn’t start for the right reason.

Solution: I got there in the end.

When people ask me how I got involved in real estate, I usually mention that I was a reluctant participant who turned into an accidental landlady. My college degree (true love) was English. But we all know that sitting around quoting Shakespeare does not make you money and makes you an object of pity and ridicule in all social circumstances. I had started a career in handling workers’ compensation claims for coal companies and other industrial employers to keep from working at the mall like many of my other fellow English major graduates. Since my husband was busy in school and the firm where I worked paid for graduate classes, I got an MA in English (just to really amp up the overqualified and under skilled for all jobs factor) and, more usefully, an MBA.

I then managed to segue into teaching college courses in writing, leadership, and business while I started having children. That was definitely a fun time of life—I love talking to people and weirdly love grading papers. However, that career does not pay well, and since I had two daughters and another one on the way, it was getting harder to keep up that pace for barely enough money to pay for childcare—you guys know that old song and dance. My husband was finally out of school but embarking on a very busy call schedule that meant someone had to be more flexible. But I’m also not the type of person to stay home all the time with small children (sorry, girls!). I wanted to do something, and I wanted to be away from my kids for part of the day.

So, while I was still teaching, very pregnant, and running kids to preschool, my husband brought an idea to the table. There was a junky duplex adjacent to his office. He thought we should buy the property just in case the office decided to expand or needed more parking. The woman who owned the property had health problems and was going through a messy divorce; therefore, we could buy the place for a great price. The units were rented out, so we could just continue that process until we could tear the building down and do something better in that area.

That was 20 years ago, and we still rent out that duplex and have added another 400 units, including commercial, self-storage, and apartment complexes to the mix. Thus, I became a landlady with some reluctance and by accident since I thought we were going to build a parking lot or develop another commercial building. My first mistake was thinking I had no interest in real estate. And the second was thinking that I had no business entering this career since I had zero real estate qualifications. You, reader, have already corrected my first mistake. You picked up this book because you are interested in owning and operating real estate. Secondly, you may even have more qualifications than I did at that time.

I didn’t start down this path for the right reason. In fact, I thought I was on another path altogether—reading papers, developing curriculums, and raising three daughters. And when this path opened, my husband and I both thought of it as just securing some land next to his office building.

While we embarked on real estate investing for a different reason, it all worked out in the end. The good part about the real estate business is that there are a lot of options. If it doesn’t work out the way you planned, you always have the option to change the plan.

We actually changed our plan a few times. First, we bought the property to have parking for a medical office. Then we realized that putting another building in that space might be a good idea. Someone contacted us about the construction of a building to house a wide open MRI business. We signed an intent to lease and got plans made. The investor backed out; we pushed him to cover our costs, and a $15,000 check later we were still there with the duplex and tenants and our squashed dreams. Then we thought about altering the plans—to build new residential housing. I still have those plans and think about that project. At that time, the. of the project was stalled by having to charge a rental fee that was too expensive for our area. If I win the Powerball or Mega Millions, I’ll revisit the idea. In the meantime, we were stuck with units to keep renting out and had to figure out how to make it work to pay the mortgage.

Some people would hear the story of our purchase and think of me and my husband as failures. In fact, we failed three times: no parking lot, no commercial building, and no new residential complex. We had already moved out all the previous tenants because we were looking to break ground on a new project. And to add insult to injury, a massive flood occurred in our town in the wake of Hurricane Ivan, creating a huge mess right around that building, inviting in river rats and leaving us with flooded furnaces and moldy basements. I’ll admit . . . it looked bleak. But Todd and I like to read books about famous entrepreneurs who have failed a few times before making it big, so we knew we just needed to forge another path. As Nelson Mandela once said, I never lose. I either win or I learn. We chose to consider these failures learning opportunities. And as Chumbawamba famously sings in Tubthumping: I get knocked down/But I get up again/You’re never going to keep me down (which is a good mantra for all landladies to remember when things go poorly).

It’s ironic that we literally just went back to renting out those same units and that is what put us on the path to our current real estate success. But without those other experiences,