I am hoping that I don't need to repurchase the same list frequently to renew it.

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

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.

So my tenants use the app pretty frequently on their own.

My highest priced rental did end up turning over more frequently to people building or buying.