Nobody can ever answer this question for a broad audience.

I try to match the lease term, frequently 10-30 years, with the loan term.

My problem with this approach is that my target audience is only those searching for managers, which is only a very small percentage of Airbnb owners since most owners are convinced that managing the property themselves is most logical and profitable.My approach is to try to target those who don't think they need a manager, and to try to explain to them why it's worth considering.

So he will be frequently in the new place but when it is rented out with airbnb he will stay at his other apt. 

Frequently, vacation rental rules differ if the residence is "owner occupied" remember depending on the state "owner occupied" can be as little as 2 weeks out of the year.

(Apologies for the late reply, I don't frequently browse forums..

They are not as frequent as it was in 2013 when I started, but I'm not conducting as much outreach as I did in 2013. 

Hi @Jason Muth, my company frequently acquires these types of projects (though we have our hands a bit full with some of our existing projects in Concord and Manchester right now) including in the area that you're talking about. 

I feel like in this market I need to move fast and offer frequent - especially where I'm looking north of Boston.

I'm not sure Hendersonville/Gallatin is your shipping container apartment captive audience.