He sees me as a dreamer, and not a doer, which to his credit is kind of accurate.

We had success in summerlin with insurance company paying .. over a 24 month period we had 3 tenants   fair market rent at the time was about 2200 or so non furnished.. we got 4100.00I did not like the turnover so I put it up as furnished rental and got 3500 and its going into its second year with a superb tenant. so seems like a happy medium for us.. 

1) 50% rule is a well accepted generic approximation 2) hundreds of underwriting has shown it to be fairly close for my underwriting for a SFR purchase in San Diego.  

So I would suggest keeping your STR property geographically close and doing as much as possible to keep your profit% high as possible.As far as the actual house you use, I would just say - be honest, be fair and strive for the best area, most amenities, cleanest house, best communication, and any other extras you can get.

At worst, fair chance of some quality mentors. 

If Don fails to pay, the bank will certainly go after me, it will at least ruin my credit and will likely take me to court.

In my market, which is a fairly economical place to build, I am friends with full time builders that are in their properties about $150k/door for construction level finishes.  

While not my main area of practice I represented a Brooklyn credit union lender, some buyers/sellers and a few landlords in real estate transactions and rent arrears cases.While we had successes and some failures along the way I ultimately concluded that I wanted to do something different with my life and cashed out of the business.

it is a fairly good start.  

Fast forward 20 years: I now have money in the bank, excellent credit, live modestly on my own, and run a business that’s doing well.Unfortunately, I wasn’t able to save much for retirement during most of my life.