How hard will it be to bet appropriate permits for the alterations (2 rooms and bathroom). 

Established developers with a history of successful projects are generally safer bets. 

:) Cant image how small the window is to play an outdoor sport on a court in LV.... 

Right now I would imagine you're best bet is a small balance Freddie or fannie loans depending on loan size and location.

No current liens but these properties have tax deeds, not warranty deeds if that matters.That as-is value is going to make obtaining financing more difficult for sure.Financing options drop off pretty steeply below a certain dollar amount because foreclosure costs for lenders can be significant.Your best bet may be to connect with some local private lenders (local investor meetups/referrals are a good starting point for this) or local banks.

You best is bet is usually to match existing.  

It's a bet on the future appreciation, maybe generates enough income in the meantime to pay taxes and insurance, chances are no cash flow. 

I would bet the attic is the 3rd br so it's really about 1k- 1200 sq ft overall. 90% of the props in all of Cleveland have converted the attic to make it a 3 br.

Any well-run NOO STR close to the nightlife/universities/sporting events does well, along with medium-term rentals for travel nurses, people giving Nashville a "test run", etc.

Two lessons I have learned: 1) CashFlow is critical and 2) Sometimes it’s good to sell when things are going well- I bet you weren’t considering selling when it was worth $2.7M.