This is what I think... and I may be very very wrong, but who cares...EVERYONE needs a roof over their head.

The current first is for $102,000 but they do not want to give the borrowers more money to payout the property taxes or fix the roof- that's why have are looking for someone else.I agree that the risk likely outweighs the reward. 

And is it a bad time to get in with home values through the roof? 

According to the inspection report, there are 3-4 layers of existing shingles under the newly installed roof.

I don’t know about the roof.

Your Cap-ex number is just a shot in the dark without knowing the age of the roof, mechanicals, etc, but $200/month is probably fine.4) Investments usually require 25% down.5) Closing costs are waaay too low.

A new roof or furnace, for example. 

I'm selling it for 10000. i asked buyer to pay all closing costs with the cheap price im selling it for (the house is in rough shape but not as rough as comparably priced properties in the area most of those have a bad roof or foundation and this one doesnt its livable actually ).

If the systems like the roof, furnaces are new, I may make a different offer on the property than if they all needed to be replaced. 

Especially if he thinks of you as a friend... and a homeless vet that wants to work to keep a roof over his head sounds like someone I wouldn't mind being friends with.