As Charlie Monger once said: our operating assumption is that the USD is going towards zero. 

In Pittsburgh, where I live and operate, this would be a two to three-month process in front of almost all out local district magistrates.

We're relatively new STR owner/operator in Highlands and have been very pleasantly surprised with demand even outside the peak summer season.

Supplement this far simpler entity approach by ensuring you have appropriate types and levels of insurance, you operate your business in a manner in which your conduct is not considered an exclusion in your policy, you work with licensed and insured vendors, you execute contracts with indemnification clauses with these same vendors/ require additional insured status &  maintain appropriate licensing and permits.

But the "art" really only comes with time in market and a deep understanding of both the market and the operations of assets.

Most lenders will vary how aggressive they will get based on the experience of the operator (you), but I don't know any that will lender to someone who's never done a spec build like you're contemplating.

I operate 14 properties from the same checking account.

No lending institution or bank would be permitted to operate with those ratios.

I added a pool and did some landscaping and have been using it as a family winter retreat and renting it to a STR operator the rest of the year.

It has been operating for 2 months now.