I really see Columbus Ohio as an extremely safe bet for the next 10-20 years.

It is currently a tree farm.The area is popular for vacation home owners from Chicago.

If you are able to self promote on social media, that might be your best bet.

I am also willing to bet you dinner somewhere that the loan docs on the underlying mortgage have somekind of prohibition on doing exactly what is being done. 

So I think my best bet to start off with is to find a property management company.That said, I’m wondering if anyone has tips on property management companies they would recommend, and/or any tips on how to find the best property management.

Nest seems like a good bet, but it's not clear if they are compatible...?

It is the most popular software in the industry and all CPAs know how to navigate it which is nice.At the bareminimum, you should do the following to make your bookkeeping easier:1 Dedicate onechecking account and credit card exclusively to real estate.

I’m willing to bet most investors here would not do something like that for fear of harming their reputation.  

I am willing to bet more than 80% of the people trying their "luck" at REI fail, miserably.This obviously tells you something truly is wrong with this niche/model!

Your best bet is hire a local designer.