It is also important to make sure your unit is up to par.  A

I have used Casa Financial Services in So Cal (mailto:[email protected]) but do not know if they can help in Connecticut. 

I designed and installed a couple of hybrid 2 stories one of which we use as our vacation home ,"Casa de Aire y Sol".

Was this Casa del mar or the Victorian?

I think the one near Reptile Gardens is Wee Casa, and I believe they are planning to do STRs. 

It can be done.If I didn't mind the Arizona summer heat, I could do the same thing there in a place located in Casa Grande Arizona for a bit less and have better access to airports for travel.

Looking at your profile I was supposing the house would be in Casa Grande.

The "West 40 Arts District" near Casa Bonita.

The best deal is if you go north of Tucson into Casa Grande or even Florence, Coolidge, or Maricopa you can buy a new build for just over $300k and will rent for just under $2k per month, you are able to get a lower interest rate on these than you can on anything else because the builders have their own lenders that will buy your rate down, so you can break even on cash flow in year one if you put 30% down. 

You may have enough to swing 1 entry level 300k house in say Casa Grande, maybe.