If I am correct (sorry if I have that wrong), there isn't a big win in it for anyone, even an underperforming asset, to help someone get some experience on their listing.

Where is the win for them? 

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

While slow and steady does win the race, your plan would be reeeealllly slooowww.

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?

You don’t win by moving your king around recklessly.

My state is very fair to landlords, but there's no way to win this scenario.

If you can network and find local players (FB groups, meetups) that could help speed it up

instead of a lender try to find a capital partner and share the deals.. thats what I do provide money for JV's  works great its a win win.. your going to waste your time trying to find nothing down lenders.. unless you already have one that really loves you then its possible.

It's very hard to win with low money down in Northern NJ.