Ultimately, it depends on what you want to do, and it is great that you are even weighing your options at this point. 

Best bet is to take a look at The Ultimate Guide to Grading Cleveland Neighborhoods and assess how you want to move forward from there. 

We considered Newburgh but ultimately decided against it. 

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

Ultimately, you want a CPA and Quickbooks...that is the magic combination.If you are looking at financial modeling or more sophisticated solutions, we use a VA Firm called UpWork...some pretty bright folks out there. 

As much as I'm all about FIRE (or at least the FI part), I do not believe that I can contribute 100% pre-tax and ultimately convert at 0% over time based on my individual situation (my buddy on the other hand who is planning to do this is in a different situation and it's POSSIBLE, but in my opinion not PROBABLE long term).  

It's all about job creation, which drives buyers and ultimately deals that matter to those in real estate.

Ultimately, my goal is to find investors to help guide me through the wholesale process and steps.

I guess at the end of the day though, if the vehicle has a malfunction and is the ultimate cause of an accident, that would always come back on me as the owner

If you're doing research on Cleveland you'll want to check out The Ultimate Guide to Grading Cleveland Neighborhoods.