Would this be an optimal win-win for risk reduction + tenant satisfaction?

Betting on future price appreciation and equity growth is just that "betting". 

That would go in front of a judge and the person with the most evidence or most convincing story will win.

You like the guy because he shares the same struggles you do, job, family, kids… why not help his company when you start REI, is a win-win?

That said, the right team on your side can make the permitting process and inspections far less painful.I’m curious... as you refine your plans, how do you see yourself balancing the home’s original character with these modern upgrades, and which element of the design do you think will win over the pickiest buyers? 

The re-vitalization of Flagler st by Moishe Mana, the big bets billionaire Ken Griffin is making on this city, brightline train, the Beckham soccer stadium will be ready for N America World cup 2026, the double decker hwy $840M Signature bridge connecting downtown miami and miami beach and the 30 acre park underneath it. 

So the Janitor usually wins, defined as making more passive income than your expenses, because his expenses start off so low and stay low.Unfortunately, after you play it a while, you get to know what to look for, like when that one stock becomes available for, I forget, $3 or something ...

Also a local eviction attorney claims the LL winning rate in evictions is near 100% even with the friendly tenant laws.  

You probably don't need much to win.

Would this be an optimal win-win for risk reduction + tenant satisfaction?