I would keep the brokerage account and focus on the tried-and-true practice of saving up for a new investment.

I'm not underestimating the work and unique set of challenges that come with it by any means.

Zachary,Your concerns about Cleveland are valid—high property taxes and stagnant population growth are definitely challenges to consider.

Even if you only averaged 2.8% appreciation annually, which if you've had it 20 years I have no clue how that's true given prices have well more than doubled in that time, youre skipping over the fact that you have been benefiting from that appreciation on the ENTIRE house, not just the % you paid for.  

It's been hard to find good property managers—I think that's true anywhere.

- Do you think it’s worth challenging the appraisal with Kiavi, or should I just cut my losses and move on?

True off market deals take time and if you have time to burn then the driving for dollars and cold calling can find you a deal.

I know some might disagree.The challenge is if someone applies and meets all your criteria and you reject them, I would hate for you to end up in some legal hot water.

So, I'm looking to invest in other markets and trying to focus on one or two so that I can build knowledge over time, but narrowing it down is a challenge. 

Demographics tell the true story.