It's a 1/1 with two car garage on a half acre composed of two Tax lots.

I would focus my research on properties that can bring an enjoyable experience to guests, such as nicely renovated house near lakes/state parks/national parks, with amenities like deck and perhaps suana and pool, also a bigger house that can host more people/pets/cars.

Do the residents have cars?

I would assume that the fire marshall would not be pleased if they saw this mess...Lastly, just from a common-sense perspective, if someone has so much stuff that it's stacked to the ceiling and spilling out all over the yard, then that's an unreasonable amount of stuff, and it's time for the tenant to get a storage unit (or rent a larger place).Think of it this way: If a tenant owned ten cars, you wouldn't let them park all over the yard and take up every parking space.

Normally our issues revolve around changing a price.  

Given thatmany tenants will make their car payment before their rent payment, we’ve copied the mortgage industry’s methodof debt-to-income (DTI) ratios.

Single family home, 1250 sqft, 2 bedrooms, 1.5 bathrooms, plus a 2 car garage.

He seemed willing to do whatever to get the unit, putting up all the money for a year and extra security deposit, but he did sound a little "car salesman" so that didn't work in his favor.  

(Higher than normal rent.) and I will give you the option to buy the property in 5 years for selling price minus x, maybe minus some of Y. 

Start with getting rid of high interest, “dead weight” debt ( cars, credit cards, personal loans, student loans, etc.).