Consider hybrid strategies, such as mid-term rentals, to bypass stricter STR rules.Engage a local real estate attorney or consultant to identify flexible markets and ensure compliance.

After he teamed up with a local intermediary in the Bay Area.. from what I read in the Wall Street Journal, Lockton has been helping investors streamline these moves.. he ended up freeing enough capital to invest in a mixed-use building in San Antonio that we’d been eyeing for a while.I’m no attorney or CPA, so I’m not giving legal or tax advice here, but there’s definitely something to be said for repositioning your insurance to fit your broader investment goals.

I am just looking for insight from local MA realtors, attorneys or landlords regarding what my typical monthly expenses (if any) will likely be (I don’t mean one-off expenses like roof repairs). 

I would strongly recommend spending the money to meet with an attorney for an hour before you put anything in writing to your tenant.Good Luck!

You're an attorney who wishes to represent people in the purchase and sale of real estate?

Find a good landlord/eviction attorney that can help you draw up a lease, and help with any potential problems or disputes that arise.

You'll have to get a contract prepared by an attorney.

. :) I wanted to go with Chase bank too for the same reasons you did, however, my attorney warned me that he has had multiple clients who had to go through endless hassles to accomplish their goals with them.  

Also, it goes without saying that if you make a procedural error (very likely as the process is designed to trip up the unsophisticated landlord, and all tenants have the right to a pro bono attorney), then you have to start the process again from scratch. 

Also, make sure you’re talking to your CPA and attorney about taxes, investment structures (LLC, etc.), and local landlord-tenant laws.