Making him turn into a landlord may be tough if he hasn't had much exposure to RE or doesn't want part of it. 

This gives me 60 days that the rent is being paid to find a new tenant, which is usually enough time, and a bonus if they move in before that 60 days is up.

Thanks in advance You might be even be able to take 100% bonus depreciation this year or take de minimis expense to deduct the entire expenses this year. 

I'm open to suggestions, bonus points if there is a non-stop flight from Boston. 

If the numbers are as good as you say they are there should be plenty of room for both of you to make money and you have the added bonus of walking away with a ton of new knowledge. 

I know I'm not counting appreciation but I see that as a bonus.

I got worse terms than a individual loan sure but starting the long term relationship now is worth it for the future business.One bonus was the commercial loan had no “seasoning” requirement because I bought the property for cash, then went to them for the loan.Banks under 5-10B in market value.

I opened about a card every 2-3 months for sign up bonuses [travel hacking is life]. 

I often break it down into the "five pillars" of protecting your assets.1st pillar is avoiding unnecessary and risky activities (don't drink and drive, insurance generally won’t cover your poor decisions) and take good care of your investments - these simple steps will help you prevent lawsuits before they even occur.2nd pillar is a good insurance policy as that cover the majority of your exposure.

Thank you @Johnny Sung:Yes, I am planning for buy & hold with no planned appreciation (appreciation will be a welcome bonus :)).