I would never count on a tenant to do any work, you can't count on them and then you end up with situation like this....I can't see how a cut cord could cause $5000 worth of damage?

If it wasn't planned, potentially causes more problems (like an automatic garage door opener), doesn't add value, doesn't need to be done, I don't do it.If it's a long term tenant who I know, like and trust and they request something, I might be more willing to consider it.

He can no longer make a claim on his roof, or any damage that could be caused from an issue due to the roof, his carrier has the option to non renew his policy at renewal (this happens annually) and should he go looking for another insurance provider the new provider will have the data about the claim and know that the roof was not replaced which lets the new insurance company know a few things. 

Any concerns on your part as the buyer / borrower that might cause problems closing?

This has caused me to continuously go back and forth with my decision.

It sounds like a headache, so I'm trying to decide if we should consider 2 loans instead of causing ourselves a big headache later.Is there a post here that I can find out more about this?

What would you think about a back charge causing them to compensate you for your longer hold times?

I hate that new people come in and cause a bad name for legitimate investors who choose to wholesale occasionally.

Tenant agrees to repair any damage including that caused by the act of moving.

Im moving to Austin and housing is so expensive I figured this would also cause some homes to foreclose as well, but i see things like pre-foreclosure, shefif, foreclosed.