Operating in the Luxury SpaceWe focus on properties in the $1.4 million to $1.9 million purchase price range, which allows us to sell finished projects in the $2.5 million to $3 million range.

Because with an HOA in tow that means your not doing it alone, you have active "partners" who will be taking care of a slew of things so think of it like training wheels. 

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.

The operator may trade off the longer term benefits to keep a high quality tenant in place.

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.

I agree with Miguel, build your system, then hire a virtual assistant and train them how to use it.

The best way to think about it is you're in the business of renting a property-that business isn't operational until it's ready and available for rent (aka in service). 

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.

If this is correct, how much are you cash flowing each month after you pay your operating expenses and make your loan payment?