Frank , I don't know the details but I am closing a DSCR Monday 7.25%  885K loan shop around I don't like to change lenders but it is a numbers game.I/O for my buy and hold I love I/O,  you are in control of the monthly payment.

If the free rent were considered a gift or was taxable that could be a complication.2.

Biggest Mistake is putting all your effort into a deal where the borrower is not even fully on board or shopping mid-process.

A lot of borrowers shop blindly. 

And what questions should I be asking when I start shopping for a loan?

Have been looking into Commercial Retail shops, laundry mats, etc. but I am a bit unsure how much I could "purchase" with my current cashflow/down payment.

Of course we all want the best of both worlds; that is a hidden gem on a secluded/private beach, but close enough to a town to find good eats, drinks, and shopping.

I live in North Myrtle Beach, have a large STR rental house in the Cherry Grove section of the beach, and frequent Myrtle Beach proper often for dining and shopping.  

You might get a gift of seller concession, but putting money into the deal is pretty important to most lenders.

In Denver, that's any of the numerous areas that has bars and restaurants and shops nearby.