This requires a bit more planning to make sure you never term out of your commercial mortgage during a period of time when values are not favorable for a refinance like at the bottom of a market cycle.So with sufficient foresight and use of the pro's while minimizing the con's I side with commercial financing from a RE investor perspective, but for the newer aspiring investors I will side with conventional since its financing with training wheels that favor the borrower.

Our luxury units that sleep 16 wont be getting booked at $1000/night as much anymore, but our 2 BR 1 BA bungalow will have people lined up to book it for a week or a month at $50/night. 

How did you go about getting a sufficient contract that can help me get started?

Good tenants are hard to find and I wouldn’t lose sleep over a hundred a month or whatever (after slight increase )

@Dana PowellIf you have home owner’s insurance and require roommates to get renter’s insurance that should be sufficient I believe.

If they’re at Home Depot as 6am then most likely it’s the professionals who are out there hustling, not the ones who sleep in after a long night.

It's probably safe to say that every extra layer will add to the costs but each layer will allow you to sleep better a night. 

He is sleeping in so I don't yet know if there is an injury there that needs medical attention.

Offer to upgrade the AC in exchange for a sufficient increase in rent to pay for it.

However, if He doesn't have sufficient income to qualify - there aren't any banks that will lend him the money.