This deduction is limited to the regular federal per diem rate (for lodging, meals, and incidental expenses) and the standard mileage rate (for car expenses) plus any parking fees, ferry fees, and tolls.

Do you have a big credit card or car payments? 

I'd imagine multiple smaller units would drive up revenue per sqft.I have always wanted to do rv/boat/car stoarge and toss up some good size solar panels and charge premium for covered parking haha.

The contract will renew automatically every year.

I would figure he has his house listed (hence needing a place to go), his car, his credit card bills etc.

Such a PM will be pricey, but at least you will have someone local who can handle emergences in the middle of the night without having to lose sleep or possibly jump in the car to drive 5-6hrs. 

So if your car payment, student loans, credit cards, current mortgage all add up to $500 (wouldn't that be nice!)

For me if my sale price is 500k, there is an existing house there, and I'm building a 2000 sq ft house + 2 car garage I'd like to purchase around 180k.

We tell our tenants that after the lease term ends it automatically goes month to month.

A living trust becomes an irrevocable trust automatically upon the death of the grantor, whether or not the trustee of the living trust actually does their job and converts it.