In my opinion, you might be better going from a large market like Boston to a market with some solid fundamentals to ease your way into out of state investing - if you're looking to be in NH, then Manchester is probably your best bet. 

So you could go with a traditional turnkey company or a hybrid turnkey company which involves an agent selling you properties from the MLS / Zillow / Their listings along with a property management arm in house to take things over post closing. 

owner to owner ( No agent involved) - Do you recommend, it helps save money....

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

The mere fact he is involving his Ira and has post closing plans suggests he is getting some benefit already. 

@George BrutonThink this situation is a bit tricky and off the books since he's a friend of a friend who wants to build trust and get me involved in the business. 

I'm looking forward to getting involved and plan on attending BP meet ups in our area and possibly our local REIA meetings as well.  

I just don't want to get involved in the game of supplicating to the tenant by offering to excuse the rent for the key.

That is your best bet or delaying closing by 15 days to make sure the unit is vacant.

There used to be a President there, and he was signing on clients with the promise of being "personally involved in the complete transition".