Not-so-succesful Real Estate Stories


Thanks for sharing!

How did you find your property management company?

You friends with the water tank should probably look over their insurance policy they have and see if it is the proper coverage for a rental. I’m pretty sure their is lose of rent coverage in the event of an accident such as that but, I’m not 100% sure.


I used the the realty company that managed our community HOA association. Probably not the best way to choose one long term but it worked for a year.



I found the tenant placement agent through networking. I joined a REIA (real estate investment association) and starting meeting other investors and found a couple that were of similar interests as myself. When I asked around for a referral, I got a few suggestions from a couple of friends. at the REIA Since I was looking for a tenant with a housing assistance voucher, I wanted someone who knew the system and knew the local government program as opposed to a regular real estate agent. He proved quite useful too in helping guide me through the process and even in going down to the local government offices to talk with their management about undue lateness in my rental payments. I don’t think the case agent I was assigned to was as diligent as she was supposed to be and I was due several months rent from the government at that point, which just isn’t supposed to happen with that program.


Yes - we definitely learned a lot, which was helpful when we decided about six years later to get our current rental property. However, this property is located in another state (where we may move back to in the future), so we will be renting it using Airbnb.

We would use Craigslist again to sell our current home. That being said, if we were looking to do real estate investing and set up a team where we were selling our home, then I may go the realtor route. Obviously it is important to have a good sense of your market if you aren’t going through a realtor before going that route.

Regarding using Craigslist to find tenants, I would as long as you have set requirements that you are using to screen by. If we were looking to scale our real estate portfolio, then we would more likely look for a property manager.

And I’m not sure that we would have kept our first house even if we hadn’t had a horrible rental experience. At that time in our lives we were more focused on our careers and getting back to one house felt like a relieve! Also, I think it is harder to rent a house that you have remodeled (and not specifically with renting in mind). In our current house, we know and expect a certain level of damage but it was hard to see that in a house we had invested a lot of our time and money!


This is a very inspiring podcast regarding real estate.


@SteveC You’re completely right, real estate definitely isn’t easy! People just make it look that way.

Though, the majority fail. And those that learn succeed while others do not.

I’ve got a lot of stories about failure (as well as success) on my blog spanning over a decade of experience as a real estate investor. And I’ve written books on the subject (which hit #1 on Amazon), if it peaks your interest.

Hope that helps! :slight_smile:


Oh I have a negative with some tenants I had. When they left. They trashed the place. I sued in small claims won a judgement. They appealed. Didn’t realize you could bring in attorneys on appeal, they did. Judge lowered the amount. Hired a collection agency, put lien on a new home they bought, then they filed for bankruptcy. House didn’t count. Had to take lien off. Received nothing :cry::cry:


I bought a house during the real estate crash in 2009 cheaply.

But the house was built in 1950s, poorly maintained. So I had to invest a lot: clean mold from crawlspace, replace roof, replace concrete driveway, replace appliances, doors and windows, remove sick trees. In the end, even in 2017 recovered market, I lost plenty money when I sold it.

So lesson learned - assess how much repairs will cost.


Bought a duplex in 2007. I had great tenants for a while. in 2012, both units were vacant and a family needed both. Their credit reports and W-2’s were all on the up and up.

Fast forward 2 years, they don’t pay the rent. Their chinese buffet restaurant is shut down. I walk into the property and there’s 8 bunks (16 beds) in each duplex. Place was completely trashed. Bathrooms were ruined. Kitchen was never cleaned…cockroaches everywhere.

I fixed up the place and sold it. Biggest weight off my shoulder. I moved to real estate crowdfunding…so much easier!


My parents had a real estate investment that ended up losing value and the tenant that occupied the property couldn’t afford to pay the rent. We had a hard time evicting them because they filed for bankruptcy. If my memory serves me correctly I think they lived there for free for almost a year! That was pretty crappy.