Landlording & Rental Properties

The Smartest Way to Become a Successful Landlord (Hint: It Involves a Field Trip!)

Expertise: Landlording & Rental Properties
10 Articles Written
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“A wise man learns from his mistakes. A genius learns from the mistakes of others.” —Unknown

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Real estate investment courses are a dime a dozen. If you've even thought about becoming a landlord, you’ve already been flooded with ads for them. However, the best education you could give yourself is from the school of hard knocks—or even better, from observing those who “are enrolled.”

The best part? This type of education is FREE. Just go hang out at your local courthouse.

Every prospective or new landlord should consider sitting in on some cases to be required training. Take a field trip to landlord and tenant court in your property's jurisdiction. If you're serious about investing and stick with it long enough, you'll end up here eventually.

Make sure that your own case is not the first time you’re learning the ropes.

Related: My Botched First Eviction (Or Why You NEED to Study Landlord-Tenant Laws)

The Benefits of Observing Landlords & Tenants in Court

Benefit #1: Learn from the mistakes of others.

By observing other landlords and tenants in court, you will begin to see what (and who) to look out for in brilliant, technicolor, 20/20 hindsight. While you are watching other people have a very bad day, you can sit back comfortably, taking notes.

The majority of cases will be landlords suing their tenants for unpaid rent and heading down the road to eviction. What might these tenants have looked like on an application?

You will see tenants not show up; you will see tenants plead for charity. You will see landlords hurt their own cases, and you will likely encounter the notorious professional tenant (as some call them).

couple on laptop, on holding gavel, online auction concept

The professional tenant is very savvy about the legal system and pushes their rights to the limit of the law (and beyond), making your life as difficult as humanly possible. They suck the life out of your investment. They prey upon your goodwill.

They are your worst nightmare as a landlord, and the courthouse is their happy place. They know exactly what to say (and not say) in order to take advantage of every loophole at your expense.

They’ve brought their paperwork and are making puppy dog eyes at the judge. Is this landlord about to get creamed? Better to spot someone else’s professional tenant there in their natural habitat before encountering your own out in the wild.

You will also see landlords trying to recover money for damage to their property. What can you learn from them about deposit amounts and related policies? You might see various other types of cases, too, such as tenants skipping out on their lease early, tenants counter-suing for wrongful eviction, landlords sued for maintenance issues, etc.

All of these types of cases are offering nuggets of wisdom to you, the observer. This is the absolute cheapest way for you to learn these lessons.

Related: Alternative Dispute Resolution: Avoiding Eviction Court

Benefit #2: Demystify the process.

There really is no substitute for acclimating yourself to the landlord and tenant court process than going yourself and seeing firsthand. Your local government website will give you some boilerplate guidelines, but they will not tell you which judges seem particularly sympathetic to tenants and which are not.

A website won’t explain to you the other faces and personalities in the courthouse you will deal with. Online, you’re not going to grasp how things in court generally work.

Meanwhile, the dreaded professional tenant probably knows all these things very well. Make sure you do also—before your own case.

European style Roman column

You also need to know how things work in your particular area. Every real estate market is different. Laws and regulations vary from state to state—and even city to city. A major problem in one area will be unheard of in another, so be sure you are observing court in EVERY area you own property.

This way, when the time does come for your case, you’ll know where to go, where to park, where to check in, and what courtroom to go to. You will show up on time, quietly focusing on winning your case.

In real estate investing, there are plenty of horror stories that do not end up in court. I hope that you start off your real estate career with consistent tenant screening practices. I hope you have nothing but nice, quiet tenants who pay every month in full, like clockwork.

I hope you never have to hear about their personal drama. I hope you can remember from the start that your investments are not a charity vehicle, and I hope your tenants understand this, as well.

However, chances are that even with the very best practices in place, you WILL end up needing the court system at one time or another. It’s never pleasant to find yourself in that position, but you will dread it less and sleep better at night if you do yourself the favor of familiarizing yourself with court.

You might also do yourself the double favor of learning how to avoid it as much as possible to begin with.

What do you think about this advice? Have you ever ended up in landlord-tenant court? Tell us your story. 

Leave a comment below!


Joe Asamoah, MBA, Ph.D., is a seasoned real estate investor. He owns an impressive portfolio of superior homes in the Washington D.C. area. With over 30 years' experience acquiring, renovating, and...
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    Judy Lintus from Conroe, Texas
    Replied about 1 year ago
    Great idea. I like to be prepared and will definately be checking out the county courthouse for a few lessons.
    Mandeep Sam
    Replied about 1 year ago
    Good tip Joe, it’s always wise to learn from others mistake. Would try this strategy someday, I had one encounter where my tenants were not ready to vacate the place, but instead of following the eviction process, I followed the win-win strategy, by waiving off 1-month rent for tenants and giving them 6 months extension. Tenants moved out smoothly and without doing any damage.
    Amanda Gant from Washington, DC
    Replied about 1 year ago
    I just spent 6 months going in and out of tenant landlord court in DC. Let me tell you. I have no vacation time, and have lost 6 months rent, in DC that is around $2200/month!! What I learned: Yes, you can save yourself 2-3 months time by getting educated. Once I was in court, I would seek out to speak with other small landlords like myself to ask them questions. I would also speak with professional lawyers representing other landlords to get tips here and there. After going through this myself, I would say it’s really worth the time. Don’t just observe, but talk to other landlords and lawyers. Also, learn the process. Lessons I learned: 1) I will file for eviction after 2 weeks of non-payment 2) I will not take “continuances” as an option. Sometimes DC makes you take one no matter what, so the tenant can seek pro-bono services, but I will not accept more than one continuance from now on. 3) Try to be nice to the tenant’s pro-bono lawyers they will get. They know the rules, but can also help the (often crazy) tenant reason with reality. 4) Pay for a home inspection and get the other side to accept via praecipe the inspection as evidence. You get bonus points for keeping a tight ship and a unit in good shape. 5) Try to avoid jury trials at all costs. This might be difficult if the pro-bono lawyer is 6) Try to settle out of court. Can you pay the tenant to leave? I wish I’d have offered $5,000 in exchange for a non-redeemable eviction. She’d have been out 4 months earlier, and I’d have far more in rent. 7) Always ALWAYS require and check professional references. I did not for this tenant and it has been horrible. These are my tips. I can’t wait to better manage the next problem I have.
    Courtney Duong
    Replied about 1 year ago
    Hi Amanda, Thanks for the tips. I am a newbie and going through this right now. Tenant has been in the house for 8 months now and has been paying super late every month (except for just 1 month). So, in early June when I still didn’t see payment for May I filed for eviction because I couldn’t deal with her anymore (rent is $1700/month and during application her pay stubs showed she made $6400/month). Hearing was set at JP court for 6/24. She didn’t show up. So judge said I could come back on 7/2 to file for writ of possession. Well, on 7/1 she appealed so on 7/2 when I came the lady at court told me tenant has until 7/8 which is tomorrow to deposit 1 month of rent to court registry. If she doesn’t then I can come on 7/9 to file for writ of possession. But if she does then she gets to stay for month of July and we will have to go to higher court for judgment for eviction and payment of June. My RE agent who is only helping for free thinks I have a good case and should not hire a lawyer because that will be another cost to the eviction. However, both her and I don’t know much about this process. We just learn as we go. Many others on BP site suggest to go with a lawyer. Having gone through this yourself may I ask did you do it yourself or you had a lawyer? My agent said that if tenant doesn’t pay into court registry by 5:00 pm tomorrow then I need to go there first thing on Tuesday to get writ of possession and to ask them not to transfer the case to higher court. I get the getting the writ part, but why asking them not transferring the case to higher court? Because the way I understand it is if she doesn’t pay tomorrow then she is at default, again, and this time for good and I can definitely get my house back without going to court? Do you have any other tips that you can give? Oh, more questions: what is pro-bono? And what are continuances? Thanks.
    Joe P. from Philadelphia, Pennsylvania
    Replied about 1 year ago
    Courtney…hire a lawyer. This tenant is taking you for a ride and you have legal questions/issues that frankly, a real estate agent shouldn’t be advising you on. Tenant pays late every month…red flag. Missed May’s rent…red flag (did you file notice to quit/pay?) Tenant appeals, sure, because they want to stay in the house…red flag (have you visited and checked condition?) How expensive should this lesson get for you? I’d do one of two things — ask the lawyer if cash for keys is an option. If not, ask how you will proceed. Also, google is your friend. Look up pro-bono and continuances there.
    Courtney Duong
    Replied about 1 year ago
    Hi Joe, She did pay for those months, just super late. The first few months I believed in her stories and waived the late fee. Next thing I know it’s late every month and there is always something with her so my grace had finally ran out (and she makes $6400/month while rent is $1700/month). Yes, I posted notice to vacate on 6/3, then filed for eviction on 6/7. I did the inside inspection the week before that and the house is in good condition. Today is the last day for her to post 1 month of rent into court registry. I went there at 4:45 pm and they said she did pay today. The lady at court said that applies to July and that we will have to go to higher court for judgment. She did pay for May on 6/14. So now she only owes June. So I think I will see a lawyer sometimes this week. I will ask the lawyer how will I proceed from here since cash for keys is not an option. After 8 months of lies and never sticks to any days/dates she gave me she has no credibility to me so I am not comfortable with working with her on anything without the law involved. Believe it or not, the Saturday before the Monday I filed for eviction she still came up with lie for not making the rent so I filed for eviction first thing on Monday morning. Thanks for the tips and questions. I will keep you guys posted on this.