-Or is it more beneficial for him to sell it through typical financing when it comes to capital gains?

Hey @Dave MeyerInterested in hearing what your typical arrangement looks like.Is there upside for the owner in the form of revenue split, above market rates, etc?

Regarding your question about the deposit, typically, it is best to address the security deposit issue after the current lease expires, laws do not require tenants to sign an addendum for anything during the course of the current lease. 

Depends on how long it typically takes to rent a house in your market. 

Do general contractors typically provide a fixed price or labor only bid with flips?

Rentometer for automated valuationsCheck current listings in HotPads, Craigslist, Oodle, newspapers -- if 5+ unit try LoopnetCall For Rent signs you see in that area of townCheck out property management websites; they typically have all of their available units listed onlineOne way to get a baseline is to check Section 8 government website for the areaHave a realtor run rental comps for you

Think past the typical or the facade.

Typical average properties are getting 5, 10, 15+ offers within days..  

Not typical for investors to get the cops called.  

Pittsburgh is certainly a strong market to invest in as the buy-in is typically better than other larger, more saturated, cities.