Looks to me like your roof has been extended across the property line to dump water onto his roof.  

There's a lot of real estate investment activity in my immediate and extended family, but this is pretty new to me in terms of buy-and-hold, flipping, etc. 

If she has been a good tenant and is still paying you might want to extend some flexibility.

I would assume it should be coated with an elastomeric coating every 5-7 years to extend the life of the foam.  

I think the distinction is whether you're talking about a personal umbrella policy (which IS liability insurance, but covers pretty much any claim made against you personally no matter where it happens) or just extended liability coverage on the rental property (if anything happens at the property, you're covered).

From my observation, there always seems to be unexpected surprises during the reno/rehab that will extend the duration and increase the cost of the reno.  

He asked if there was a way I could pay him $1000 a month over an extended period instead of all upfront so he could keep his benefits.

If that doesn't work, should I try and get the contract to extend past the lease date then close?

Seller is getting very close to auction date, and Ocwen won't extend.

I would say if a deal makes sense and you don't over extend yourself then go for it.