I want to add the stability of real estate into my portfolio and patiently grow that investment and harvest the tax benefits of long-term investment.

I also have a seperate list of courthouse data, Probates, Divorce, Tax leins, Ect.

However, the self employment could (or could not) pose an issue depending on how much you pay yourself yearly and what you report on your tax returns.  

Columbus & Raleigh-Durham are both great places to invest as an out-of-state new investor Short-term rentals can be challenging and is always subject to new local registration and taxes. 

I've also avoided paying Capital Gains Tax on selling my crypto. 

To add to this there may be some tax related questions you may want to speak with your accountant about. 

It's not worth risking the invalidation of your IRA account which would cause penalties and taxes.  

The last thing you want is to buy something and the Agent's estimate on rent and/or reassesed taxes was wrong and you end up with a non income producing property. 

Regarding the secondary roof issue, your first step should be to consult with your current insurance provider.

As an agent, I scrub the tax and property records for data to find off market deals and skip trace using a combination of spokeo (alright) and batch skip tracing (better) and call using mojo dialer.