However, I've been standing on the sidelines for far too long - time to make it happen.I am a lawyer by training, and spent some time as an Air Force Judge Advocate or "JAG" (a military lawyer, for those who haven't seen the TV show), and transitioned into the federal government in the field of information privacy/security. 

Im 25, and currently in the Air Force Guard.

My water lines are below the frost line and I have an air handler that has some losses in the ductwork that keeps the crawlspace well above freezing so I never have any pipes freeze.If you have exposed pipes under the house I would add insulation or heat trace tape.

It's a 5 Br 2080 foot duplex without central air or paved driveway.

I'm trying to make this thread a little more knowledgeable for another reader since i went through many forms and passages myself. 

Word on the street is to not put long term wealth into AIR BNB with all the new legislation coming down the pike.

Is there somebody I can go to in order to create an air b&b?

No air conditioning installed, 1 window AC unit in each of the units.Currently the heating(gas) bills can go as high as $800 in the coldest months and as low as $30 (tankless water heater) in the summer months with single pane lead glass.

Since the passage of rent control, we have seen the available inventory of rental units on the island shrink.

You can even Air B-n-B your unit when you're away to really make the place cash flow.