There are great people in both roles who are totally awesome and the negativity you hear about Wholesalers does not apply.

The thing is there was a lot of appreciation in 2021 and parts of 2022.Real estate didn't appreciate(in general) much from Summer 2022 to start of 2024.In general, the investment, while lagging behind the stock market return, is not a bad investment.You got 10% cash on cash return in year 1 and 8% cash on cash return in year 2.It was negative in year 3 but that is okay if you beleive it to be around 10% going forward.A lot of investors are starving for cash-flowing deals so I am surprised these properties didn't appreciate much.

We've owned them for 20-plus years but the recent property tax increases have negatively impacted our cash flow as have major repairs such as roof replacements, AC units, etc.

I should have also added that the reason I am pulled towards real estate as a wealth generating mechanism (I.e. the appreciation aspect) is that I bought my first house with ~$20K of my own money in Baltimore (supplemented with 6K of grants), bought at the right time and did a little fixing it up, used the proceeds from sale of Baltimore home to get into the lower end of the market in quickly appreciating Seattle.

Chances are you may show a negative cash flow which is throwing you off.

It may not seem like a lot, but it really saves a lot of time to focus on other tasks/aspects! 

And I didn't even dive into the construction aspect and knowing what works and doesn't work for a chosen submarket. 

I do like the auditing aspects, though—isn’t that something EAs are knowledgeable about too?

He just hosted a get-together - a Family Reunion - where we took a deep dive into various aspects of BRRRR, how to source deals and a look at how he is rehabbing the hotel we were at that he owns.

If the landlord was aware of his past, yet rented to him anyway - any lawyer worth their salt would make a nexus between those two pieces of information and create a liability claim.In addition to the extreme negative press you would get, it also takes time, money and energy to defend a lawsuit you will eventually win.