But it fits with the current portfolio I hold in that town and doesn't take much extra work for the returns I get.

The tenants have paid and if someone is thinking about moving out then an extra surcharge that hits if they aren't out in time for us to turn the place for a lucrative AirBNB short term rental can help massage the move out timing.That said with MTR we do not have the cleaning costs that eat up a lot of STR gross, and its lower hassle in some ways.  

Just having an extra kitchen doesn't impact insurance eligibility. 

He demanded $2000 extra and said we had 24 hours to pay if we wanted the loan closed!

Maybe to have extra cash for repairs. 

With all of that said, my main goal is to have long term appreciation and if there is a little extra cashflow at the end of the month, great. 

You definitely would want to read through the county laws again.If you don't want the extra load up front, best to wait until you get the license.

Otherwise perhaps your winter people will pay $500 extra if your cap is $500 and that is not what your competitors will be doing. 

While state specific leases are simple and can work, spending the extra investment and having a real estate attorney help create one for you will likely create more value/protections and save you money in the long run

If you are still willing to stay in the same unit as your brother you can get a 2-4 unit building, rent out the other units and still rent a bedroom within your unit to your brother for extra income.