Just plan for worst case scenario 1-2 years of mediocre STR bookings and if you can survive this you’ll probably do well.You’ve already down the best research you can do- Air DNA plus just looking at the calendars of current Air Bnb listings in your desired area. 

I'm looking to do a vapor barrier to reduce any potential moisture, Insects, raydon, just better over all air quality is what I'm going for.

I’ve had Reccomendation a for Zillow rental, cozy, etc but Rent Redi SEEMS to be the easiest for one stop shopping.

Alternatively, get someone to manage it as and Air BnB.   

What happens when you get a tenant that likes fresh air and leaves the windows open, but also likes the place warm and cranks the heat to 80*? 

The air base is expanding significantly. 

You should start by getting estimates from contractors to determine approximate roofing, heating/air, and what other repair costs are going to be, once you have those numbers, that'll make it much easier to make a determination if the after repair value justifies the expenditures....

Im in about the same steps of the process as you, but I will say- Air DNA is very much worth the value.

Needs a new roof the AC units may have to be replaced, the building is infested with mice and rats so we might have to fix the air ducts the repairs that were done have to be redone.

with a link to fill out the cozy criminal background and Fimancial  check they pay Cozy something like $39 I state if your results are are satisfactory we can have you take a look To the people who pass that step I text back and tell them the day and time when I will be showing the property.