I am a small business owner, business is not doing too well right now so that’s why I’m looking at an all cash buy, so I can get a nice cash flow to supplement.

He also doesn't control regulations in the states/cities, but his attempts to cut regulations may trickle down and impact personal property rights and people's ability to use their properties as they see fit.

My suggestions would be in this order:(a) Determine the type of financing you qualify for - this will short cut the process considerably and save time on investment angles and next steps.

End goal is a bit different though since I am looking to supplement retirement income with cashflow which is 20-25 years out. 

Those are repairs that we had to pay for, however, and that can cut into your cash flow if these problems occur often.Well maintained equipment is also key.

If PropStream’s data isn’t cutting it, you might want to check out Prime Tracers.

I believe that the Federal Reserve is going to cut rates by 25-50 bps at it's September meeting (no emergency cut), but that 30-year fixed rate mortgage rates will rise to upper 6s low 7s around the same time, and Commercial borrowing rates, including for multifamily, will increase as well. 

The sentiment was that STRs are a critical part of Buncombe County so they don't want to cut them off.

I recently toured a property in Phoenix where solar power and water-saving features cut operational costs by nearly 20%.6.

It would be nice if you had a contact who was an actual mason not a marketer.  1930's construction is rare so maybe they cut some corners it was a global depression.