Just know, typically, in commercial transactions, the seller is not likely to be open to footing the bill for your broker.Things I would be curious about: Why is the landlord creating and selling off, effectively, retail condos?  

The plan would be to market the bottom level weekly during the peak season and split the off-season rental monthly and weekly.

Also, 6 months reserves is a great rule of thumb, and some lenders require that as proof as well.We do have an arrangement with Helix Mattresses where I can +/- 50% off retail with free shipping on all mattresses. 

I built a number of them pre 08’ but backed off for a while.

And remember that even if the section * tenant offers to pay more than the allowed rent, it is illegal for you to accept more than the allowed rent and it could get both you and the tenant kicked off Section 8.

Got notified of an off market property already functioning as a STR... what questions to ask?

@Kirstyn Indy - I would start off by calling the credit card(s) that you wish to add your child as an authorized user. 

Or would I be better off keeping it since it’s cash flowing (been this way since day one of renting it 4 years ago), saving some more of my own cash again, and just investing that instead into a short term rental property?

I just don't allow "one off". 

If they want to sell it, then if they are truly a friend why not have them get an agent and sell it versus you trying to make a buck off your friend?