^sorry you have had such a shit time in florida. but to recommend he be homeless in a cold area, to avoid your concerns with florida, is ridiculous.
florida definitely has it's pro's/con's, like EVERYWHERE else in the world. it's what you make of it.
I didn't have a shit time in Florida. It was a great place for 15-20 years and I made enough money legally to retire by 45 if I'd wanted to quit working. I still own property there, go back every couple months, and have many close long term friends there.
However with $50 in your pocket and nowhere to go, it is a shit place. I honestly don't know of any city/town that is even slightly helpful or tolerant of homeless folks. Very much the opposite. Social services are very poor. There are hundreds, if not thousands, of tent cities. I've been a nurse for 25+ years and I've seen quite a few patients discharged to the street and tent cities who are in wheelchairs, have pic lines, serious wounds, etc. they get no help, nothing and it is deplorable to do such things to people who are seriously ill. I have seen patients in the ER who have been beaten to a pulp by cops who go into the tent cities to run people off. These folks have nothing and no information or help is offered to them.
It is not a good place to go if homeless and several Florida cities have been tagged with "meanest cities in the country" by various publications. I'll look for and post links if I can find the articles.
The summers are brutal, the bugs are beyond description, and it rains daily from May or June until October. From talking to lots of different people, it seems that many folks from other states think you can sleep on the beach, eat fruit from backyard trees, and the living is easy. This is not true at all. Many jobs have absolutely suck wages and rents are high most everywhere.
I've just seen some really sad things happen to folks who were homeless and down on their luck through my work and **IMHO** wouldn't suggest anyone in the OPs situation look to Florida as even a temporary solution.
-izzy