Both of these factors plays a role in my thinking hey maybe they would be to sell if I found a lender that can close fast and pay cash.

Effectively losing one rental but gaining two more (would move out of my current house with ADU and have it 100% rented).A driving factor is how will selling this asset accelerate you to your next goal? 

I feel like this may play a factor in how willing the county is to just get the property "off their books."

I know portfolio in my area range from 4-8% depending on a ton of factors.

None of the factors that you've mentioned are present in the area, and therefore are not affecting any kind of market shifts.The City of Naples, as well as Collier County, both have ordinances preventing short term rentals at all times of the year.

I am not against having our accountant run the numbers but would like to comprehend and give it a try myself, but it sounds like there a lot more factors into the calculation than I thought originally.

Not looking for the cheapest (although cost is obviously always a factor), but also don't need a luxury focused GC.

The 1% rule is a good start but obviously would not be the ultimate factor.

Is that going to be a factor, or does it not matter how much is owed if the seller if offering the house for 50k?

@Joseph Sapyta it depends on many factors.