He just wants to sell the house and use to $ to help his father with health issues, so he's willing to sell for under market value.

Otherwise contract a service for the season that will automatically take care of for every snowfall.4) YES you need to heat them!

Be careful, and happy to connect if you need help. 

It definitely escalates the situation though, so I'd research the process and carefully consider the option before embarking on it...but if you pursue that route you can likely escrow Dec 1 rent and I'm sure that will get some attention. 

It says you do not have to accept online certificates.We require documentation from a current healthcare provider that has knowledge of the disability.

Pro Tip: Airbnb provides a level of protection if you end up with a "problem" tenant.

This might be a rookie mindset is it bad I don't care for cash-flow at the moment in my eyes if someone helping me pay down my mortgage and build equity I'm okay with that.

I would be very very careful as this is now illegal in multiple states and considered predatory.

I know one-sided relationships usually don't last, but given my lack of experience I doubt I can be much of a value-add friend - unless you're looking for insider tips on how NOT to do some things :)  So you folks with more experience, let me know what kinds of things turn you up or down when it comes to newcomers.

Welcome to the community and be ready for a huge amount of information at your finger tips.