Best city in FL to retire in and why?

cosine

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viper88 check out www.wikipedia.org type in a town and it will give you a lot on info from history, demography and weather. i've been using this as part of my search in finding a place that i would like to check out and move to.
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Bamaprof

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I am sick of the midwestern winters! I am not digging the State of IL and all the taxes either. I don't mind paying my fair share of taxes but I want to see what I am getting. I can tell you it's not much in Chicago. Nothing but politicians getting fat on the backs of tax payers. Not to mention the crime.

People are abandoning IL at a record pace. Illinois is broke. There will never be enough taxes to make up for it. It a ponzi scheme. When the music stops a lot of people will not ave chairs. Not to mention the Chicago pension funds have been mismanaged for decades and are unsustainable. The only real solution is filing for bankruptcy or pension reform. Neither will happen because the politicians and Judges rely on the pensions themselves. They will never cut their own throats.

I noticed a lot of Jeepers are from FL. Any suggestions for areas to retire in FL? Still too early for retirement but need to give it some serious thought.

Gulf or East Coast?

Pros and cons?

Would love to be on the water.

Only visited Miami, the South Beach area and the Keys. Great restaurants and beaches in the South Beach area. I loved all of it. Something to be said about flip flops and shorts year around!

The Miami South Beach area has a lot of condos on the water and is appealing but I wonder if the real-estate there is in a bubble? Some people tell me all the beach front condos are inflated due to huge influxes of wealth escaping South America?

I love the Keys. Key West was so relaxed. Weather is great when it's not hurricane season. The other downside may be all the tourist if you actually live there? And of course cost.

I have friends who live on the Gulf side in the Tampa area. They live there because they are military. They said they would consider the Gulf side further south. I believe Sarasota was mentioned?

Suggestions for the East Coast?

What about hurricanes and storms? How often? How is flood insurance? Originally I planned on buying, about a $500K-$600K budget. I am considering renting first now. Someone else recommended renting full time because of hurricanes? How do you deal with hurricanes?

How about health care on either coast?

Advice?
St. Augustine! Less crowded, more distinct 4 seasons, beautiful, historic, Jacksonville and Orlando short drives.
 

Buckster

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I'll throw my .02 in.
Wife and I are ready to get out of Charlotte and head south. Boss gave his blessing for me to work remote, and wife was on the 3rd interview for a great position - then covid19 hit. All hiring suspended, can't show our house to sell, can't travel to look at houses, etc.
Definitely want gulf side, not too crowded but proximity to city if we want, so looking hard at Sarasota. Good job opportunities for the wife, can drive into Tampa if the urge strikes, has a decent airport (I travel a good bit) and plenty of water access. Will be selling our ski boat and already have a center console picked out.
We will likely rent for period of time to get familiar with the area and see what we can afford. Ideally would like a canal side home with a boat lift, but insurance and tax is a concern. No state income tax in FL so that will be an immediate raise.
Not concerned about heat/humidity. Have been to the keys many times in July/August and acclimate quickly.
Anyway, reading through this thread it sounds like there are several of us with the same ideas.
@cosine and @viper88 - good luck and keep us updated on progress.
 

Kluk Ztopolovky

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I have spent some time in FL and I am thinking how much more I enjoy the West in so very many different ways. FL gets oppressively hot and humid in the summer , it can be very expensive if you wish to live in a nice decent neighborhood and good luck seeing a hill .History and people of the West are way closer to my heart than the I wanna look rich , I wanna be slim , I wanna be vegetarian and I wanna just hang on the beach for the rest of my life , sorry but that's so boring.
 

Buckster

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I have spent some time in FL and I am thinking how much more I enjoy the West in so very many different ways. FL gets oppressively hot and humid in the summer , it can be very expensive if you wish to live in a nice decent neighborhood and good luck seeing a hill .History and people of the West are way closer to my heart than the I wanna look rich , I wanna be slim , I wanna be vegetarian and I wanna just hang on the beach for the rest of my life , sorry but that's so boring.
OK, you do you sunshine.
 
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