For commercial buildings, be very specific - price range, $/door max, unit count, unit mix, part of town.

I would imagine most attorneys located around the MA, NH border area plan to make more than $200,000 per year.

With the exception of building a trailer on the property (these are hard to finance), this sounds like a good plan AND if you are using it for your business AND your business pays more than 50% of the rent (if you have more than 1 tenant), then this is a more financeable property in the eyes of banks and credit unions as it would be consider a commercial "owner-occupied" property. 

Quote from @Mel Kirchhoff:Some specific questions I have:• Should it stay fully stocked like an Airbnb (plates, utensils, towels, etc.), or pared down?

I had a similar strategy with my first few house hacks: buy in great A & B Chicago neighborhoods....get by with minimum cash flow, and wait...What's your plan for the next purchase Michael?

Just as an aside, both plan to keep their owned real estate and lease it to the business buyer.I like that because it makes the business much easier to sell.

do you know how to read building plans or permits?

If you have any specific questions, I’d be glad to help!

For example Hospitable has a option for this through there direct bookings payout sections but it is only for specific states.

Here’s how I approach niching down to a specific audience:Analyze Your Market DemographicsStart by researching your market to identify who is booking short-term rentals in your area.