Outcome 2, you increase rent by a fraction for year 1 and have the opportunity to increase to market value after year 1 with a new tenant.

I didn't hire them because I would have had my handyman board up the house for a fraction of the cost. 

You could take a fraction of those funds, dive headfirst into wholesaling to generate that kind of income.

You will have a certain percentage of tenants who will think they can't break a lease and stay even if they really don't want to - but - they are not going to be happy tenants, which usually equals more work for you anyway.I just don't think the fraction of tenants who will comply with a lease simply based on what is written in it will outweigh the benefits of a M2M contract. 

So I don't get to call that new roof an "expense" - and I only get a small fraction of the amount I paid as a yearly tax deduction.I'm a lot more chary with loans for my personal stuff.

The returns are even better than multi-family, and you can get invested for a fraction of the price.   

The spreading of any such advance…for the purpose of computing the rate of interest shall be calculated by first computing the advance…as a percentage of the total stated amount of such loan….This percentage shall then be divided by the number of years, and fractions thereof, of the loan…according to its stated maturity date, without regard to early maturity in the event of default.

It allows them to size their portfolios much faster as they only need to save up a fraction of the total project costs instead of the entire project costs. 

I can't find the others atm, but Google "fractional real estate ownership STR / rentals." 

You'll be a fractional owner.