I was willing to pay up to $1500 a month, and I am currently working. I am a computer person, which I can do anywhere.
In buffalo New York you can find a whole house for that much
Serious question.
If you have to choose between CT and FL, why would you even consider CT for the winter?
https://www.zillow.com/homedetails/208-Magnolia-Ln-Narrows-VA-24124/107895218_zpid/
$65k. 30 minutes to Blacksburg, 20 min to Princeton WV. Hospital is 15 minutes away
I strongly suggest any state with no state income tax, then.
There are plenty of inexpensive places in Texas, Tennessee, and Nevada that would be low cost and have solid Internet (and no taxation of your income).
In Texas, look for a sparsely populated eastern county, as property taxes will be substantially lower, due to how a court case came out 20 years back (it made higher income counties pay school taxes for lower income counties). As you can tell, we looked into homes, there.
As a computer person, it is very hard to find a job now. The Indians have taken over the tech recruiting market. And they wont hire Americans. This is what is causing a lot of homelessness. And it is something we are not allowed to talk about. I am in the same boat. So I enrolled at the university. Student loans and grants have kept me off the streets.
$1500 still goes a long way in flyover country. Look around on Zillow.
You have freepmail.