I agree with @Aaron Zimmerman—setting up your chart of accounts to align with Schedule E/1040 or 1065, depending on your type of entity, will again take some of the heavy lifting come tax time.

I'm just curious about, in the ballpark, how much these will cost with basic stuff. 1.

And yes, you could engage with a Turnkey company as well. 

First I would make sure where you are building allows STRs with no or few restrictions.

Find a good lending partner that is comfortable with lower property values both on the purchase, as well as knowing a group or two that can financing projects under 100k on a 30 year fixed.

The property is worth exactly what it is with zero STR rental income.

Certain lenders can accept higher than 50%, and may be able to execute even with an exception. 

Is there anyone out there with any advice?

I generally went with private money first because I’d get better rates and terms.

First it was with Citizens insuarnec, now with Menatee insurance, before Citizens it was SLide insurance...He said Citizens changed my policy to Menatee.How come Citizens does not change policy on the house we live in?