I stepped in and negotiated these all out for them. paying a bunch off foreclosing on a bunch etc etc. they got out of it by the skin of their teeth but lost ALL their money.

On the surface this looks good but there are things you haven't considered. 

If the deal is too thin to support a hard money loan and/or there is not enough borrower skin in the game to recoup your capital if things go awry, then you can lose money just like any other investment where capital is put at risk to earn a return. 

Personally, I wouldn't invest w/ a first-time lead who has no "skin in the game", and prefer that even seasoned deal sponsors have aligned interests via their equity investment.  

I was watching a video recently from a manufacturer of edm roofing, and they were showing it being installed on a wood surface as well.

Good Credit, guaranteed money back, skin in the game (money down)????

It needs 50K in paint, central AC, pool drain, clean and possibly re surface.

But on the surface, it looks like tenant issues and long term leases.

When I lend money to flippers I insist for them to have a skin in the game.

Structures are like people in that the inner condition is reflected in the outer condition, thus any readily apparent deferred maintenance is a harbinger for more problems waiting beneath the surface.