He cant pay his mortgage now, and when he cant make rent to you later, you will be in the unfortunate position of evicting your friend. 

I always say/said  your markets are more akin to trading cars than real estate.. 

We were so poor that when we took a vacation, we drove to Florida from Chicago, ate dollar sandwiches at Mcdonalds, slept in the car because we couldn't afford to rent a hotel, and enjoyed the beaches during the day.Anyway, we decided to buy a foreclosed home for about $80k. 

If he had to choose between rent or his car the car would win out.Screening requires that you understand people and how they make decisions.

Not many headaches and our owners make 1-2 months extra rent every time the tenant leaves early so it's a nice money maker.

I see multiple cars parked at the residence overnight.

Heh, google search "car sales four square technique." 4 things are involved in a car sale.

Some STR are not real money makers but that sounds like they are saying outright you are going to pay $2000 for the opportunity to use it yourself and you should be happy to do so...  

If you take the time to make your own lease, you get to decide whether it's okay for tenants to park rusty, dilapidated cars on the front lawn.

I used to rent a room from a recently divorced guy who didn’t wanna give up his pole building, 40 pc gym, pool, hot tub, and classic cars.