This is not to say that you can't find STR's listed on VRBO, Air BnB, etc, but these are technically illegal within the county or city jurisdiction.

Background on the house... has forced heat, no central air, built in 1920s, recently renovated in 2010, two current long term tenants paying $825 a month + utilities each.

Your greatest liabilities in the home are likely to be the roof, foundation, electrical, plumbing, heating and air, and windows. 

Hello, Brett, I live in Virginia Beach, VA and Air BnB and vacation rentals are popular down here.

So much in the air, I need someone elses perspective on this!

I don't know about you, but I'd much rather spend my time cultivating my value from an air conditioned room finding deals.

I learned how to self-manage out of state while also being full-time Active Duty Air Force and the seller is looking at selling me more properties all with owner financing (Win!)  

This is COMPLETELY up in the air and speculative at best. 

if it is, only reason to add sheetrock is to increase value (for refi) and attract better tenants. look at comps in the area and see how they are done2. minisplits can be purchased and installed for $800-900 each. a standard forced air system runs anywhere from $4,000-6000, depending on the size. without seeing the house, its hard to say which is better. 3. some things i do to "tenant proof" my rentals.

Literally and open air drug market, although i have seen what investors have done in East Kensington, Port Richmond , Fishtown and can’t help but to think investors may find their way upwards.