Call me crazy, but have you considered doing air bnb in Connecticut? 

I'm an Air Force Brat but settled in South FL in 2005.

At -5° if will still put out the heat that it is supposed to, but efficiency will fall.You may need supplemental dehumidification and if you have a tight enclosure you might need supplemental ventilation.Anything you can do to tighten and insulate the building will help ensure that this project is successful.The proper way to size a mini split is to use a Manual J calculation and to use results from a blower door test as an input for air infiltration.

I assumed it was Air's problem but not sure.

I have been looking into purchasing my first investment property and one of the many decisions I have to make is going for a single family home to rent out monthly or go for an Air bnb.

Also, it might seem counter-intuitive, but don’t be tempted to overuse febreeze/air fresheners/candles/etc. when showing the home to prospective tenants.

Other items to look out for include: plumbing, heating and air conditioning, siding, hot water heater and any flooring issues.

Air B&B's not in the short term rental business, and Amazon for sure is not in the shipping business.

Lifeguards, the Coast Guard, and a LASD’s Air 5 helicopter all participated in the slow-speed chase, which took place somewhere out in the Pacific.

For now this is the plan but leaving room to add additional rental properties if we choose to expand the air b and b.