... a short-coming that I rationalize by blaming evil weather.
I am currently going through my first winter-free experience due to (legal) teleworking and leave without pay.
After 54 years of suffering through some of the worst weather on the planet, it is a very interesting datastream. I continue to be astonished at how much weather effects mood and mental health.
At the prodding of my neice, I watched a few episodes of "How I met your mother". The Canadian character referred to having an all-summer fling in Canada, and it was the 10 best days of her life. ; - )
One of the things about semi-tropical weather is the impact on materialism and social interaction. There is an endless list of things to do that do not require money to enjoy, even simply walking around the block and listening to the birds. Windows and doors are open, people are on their porches, and social interaction is baked in by simply moving around.
Television is something that gets turned on later and later, and less and less, without any effort.
One can live very very cheaply in Florida (or Arizona), if done a certain way to avoid financial traps. The tax system is strongly biased toward lower-income-employed/pensioned. Not a good place to be on county welfare, and they exploit second-home owners proportionate to the price of the property...the latter being the actual state tax base.
For SouthWestFlorida, the key is to be east of the freeway 75 to avoid much higher hurricane evacuation zone insurance charges. The economy is starting to pick up and I am seeing help wanted signs. One of course should never move somewhere without the job lined up first, (so the method is to begin with vacationing in Florida) or a very large stash of backup money, especially if children are in tow. Attractive places pay much less than unattractive places...you are paid in sunshine, but I would say for lower entropy dudes, this is a profitable trade.
Healthcare is king regarding jobs, if one is in a position to obtain a health related credential, such as a medical testing tech of some variety. Many keep gardens going year-round, with some goats on acre parcels to qualify for drastically reduced property tax.
A person on a small fixed income, not tied down to a job, could also snowbird by staying in a northern summer lake/river cabin in the summer (some find the summer heat to be oppressive, others adapt - I find heat to be uncomfortable, but not depressing) and renting something modest in Florida in the winter, which is what my maternal grandparents did.
There are hundreds of lifestyle options. Some live on houseboats and some live in converted trucks. I recommend a person thinking about this to make a long road trip from coastal Texas around the gulf to Key West, then drive up the east coast to Savannah, to begin getting the lay of the land, in January, or you could take my word for it an just focus on southwestflorida. There is a very active TMI group in Naples.