I am leaning towards a house hacking situation in a college town.

He'd essentially be providing up front cash, his name on the mortgage, and an opinion on execution.I'm leaning towards suggesting either a 60/40 or 70/30 split on the up front cash, which would essentially mean that he's paying between a $4,800-9,600 premium for me doing the work.

Hold each other accountable, if you feel weak lean on them for help.No matter how long you are clean you can not get lazy with addiction.  

Thank you @Amy BethI was leaning that way!

I'm leaning toward Opt 2.

That's not to say they can't cause damage, but it's highly unlikely to jeopardize your tenant's life while in the home.If the trees were clearly diseased or had a dangerous lean, there might be greater cause for concern, but this does not seem to be the issue here.To put your mind at ease, consider taking a drive through some other neighborhoods near your property.

Will the lender put a lean on the now renovated house?

It feels more risky to me, and right now when I feel like I'm just hemorrhaging money into this house, I'm really leaning towards just  getting it painted and floors done and start making money, as opposed to starting what feels like a major project with less of an obvious payoff (and I won't know if it pays off until 6 months from now when I can refi).

I know I will be strong on the rehab side but am leaning toward working with someone else with more experience on the purchase, and rental/sale design aspects.  

The convenience of being able to pop in and view a house I just drove past is worth much more than any costs.