Any pitfalls that I'm not paying attention to?

IF they have a high subsidy, much of it may be directed towards child care and medical expenses. 

Considering it was probation only, and he’s been approved for a medical license, and it was only a misdemeanor, I really wouldn’t give it a second thought.

Im the poor step child in this scenario who got lucky to finally get some attention.

The prices around Boston are a little out of my wheelhouse so I've started turning my attention West. 

@Alan Howard -  I think Quiet enjoyment is the main thing you need  to pay attention to here. 

I have experience with designing outdoor spaces for single family homes, monuments, apartment complexes, hotels, medical offices and more.

If appropriate, schedule open houses for efficiency and (and possibly attention).

etc.I would try to find someone in your network that can be the "elephant" to put up the down  payment and cover the rehab costs then negotiate seller financing (again considering where payments would go should anything happen to the seller) and pick it up that way.If they are concerned about their health, they are likely concerned about medical expenses and therefore a down payment of 10K and then 700/mo for 100 months might be something that they are open to.Just some thoughts.All the best!

If some major issue comes up like a fire, medical emergency, or some other incident at the property i would let my childhood friend take over the damage control by giving him some limited level power of attorney.Im not sure if there are certain limitations I can put on my friends power of attorney but as mentioned before it’s something iv considered doing.