Personally, I solely focus on my area right now because I know the surrounding towns in terms of demographics, average wealth, crime rate, climate, flooding issues, and so forth.

Based on the town hall meeting, it doesn't seem like they want to ban STRs.

When most people think of short-term rentals, they think of vacation destinations such as mountain or beach towns, often bringing them out of state.

All located in the small same town.

You can research and find out exactly which towns do or don't follow ETPA if you're interested.I'm not familiar with Long Island and New Jersey, but there may be some opportunities there as well.

I am currently analyzing an off market deal in a small college town, that is currently operating as college housing with a "rent by the room" style. 

There are always opportunities in each town.

But it would also be in the same town as my other property.

It is located in the Sommerville neighborhood and not a very nice area of town.

We may have discussed some of these previously but I'll list my ideas of your type of situation.Review the city/town's zoning by-laws to understand the allowable use for accessory dwelling unit (ADU).