My wife and I have two reliable vehicles but I decided when they were paid off to start saving right away for the next one by making car payments to myself. 

You could have sent him to collections and this would destroy his credit, which could impact his ability to purchase a home, qualify for a car loan, and possibly even cost him his job.

Normally the only time you get a number of repairs is during turnover.

I’ve had my fair share of obstacles, too, so hear me when I say this—it’s normal to feel stuck sometimes.

@Chris Seveney, it's confusing becuase you may not want to believe what I've stated assuming the NORMAL process of a closing happend. 

I strictly use them to trade into places I really want to go and I can never, ever beat the price I pay for a week as compared to normal rentals rates which are three to seven times higher per night.  

The thing is, is this normal?

I don't know any brand new STRs that hit the normalized numbers for the cabin size in year 1.  

After spending years in the car business, I decided to make a bold shift into real estate.

Now I straight up said there has to be some kind of contract and price and they did cover it with me (I don't know if they normally do that or only did it because I asked), however the price is $15k-40K or more.For me this is a major red flag and irresponsible.