RC:
Carlos from Spain:
Right, basically for vacation I like Orlando because of the theme parks for family but that is it, and for beaches I'm not going to go for Miami, don't even like those beaches full of buildings next to them, I prefer more natural beaches, less crowded, even just a few miles south in the keys its much better, and climate is hot in florida but its very humid and just gets boring quickly as you say.
My wife actually likes Orlando as well, a bit far from the beaches but she could imagine working/living there. It is definitely cheaper than the region around Miami. By living in Orlando I don't mean Orlando per se but the surroundings like Winter Haven or such. We do not like Cocoa Beach for example, it has a certain charm but we love skyscrapers at the beach and big city life.
If I had to live in Florida I would pick a small town near Orlando that has good communications (airport, good school, etc) but has more of a small town life style AND people. Never in an urban environment. The opposite as in Europe, were I like to live smack middle of the busy and active city and spend weekends, holidays on the country house near the beach. Weekday living on the country side or suburb for me feels kind of isolated and gloomy.
Less crowded? This is exactly what we do not want. We love crowded and noisy and crazy and different... 
If I want total relaxation, I get that in my coffin when the day comes. 
Different tastes
for me a crowded beach is a contradiction, its an open place to relax and not be in a "herd". That said I'm not much of a beach guy, maybe because I take them for granted but I get bored real quick on the beach and I don't sun bathe either, so I like to do activities around the beach instead.
But for actually living? not with a family, not the place I would want my kids to grow up, bad influence and doesn't matter the school or the place, its society, superficial, no good values, materialistic, and prioritizes in life exactly what shouldn't be prioritized, etc.... won't influence a grown up but a kid who is forming its mind, that is a no go. Not to mention the crime rate unless you live somewhat secluded which is not my idea of freedom, the social restlessness, drugs, etc. and its just getting worse and worse.
Bad influence comes from wrong choices and this is what the parents are for...to guide the kids. My kids are in a public school (many of our friends have their kids in an international school, which is basically a private school) and I actually think that it helps more when kids see that their good life isn't a regular thing (public school) than seeing only Porsches and expensive cars every day (private school), thinking that everybody lives the dream. One reason we sent our kids to public school because we wanted them to be in the middle of life here, not at the margin of it. It was a good decision, our daughter is close to finishing school (SAT/ACT in the US) and she is a good kid. Same goes to our son, who still has a couple of years in front of him but he is really a good kid.
I would never take my daughter to a public school here in Spain, I would do what ever it takes to avoid that. Here you can't control the teachers which are mostly leftist or don't respond to anyone, don't want to sound elitist but the peers is also an even bigger factor, in public schools you have bad conflicting students in the system, you have immigrants who don't know the language or customs and slow the class, you have less mannered and educated kids, even some violence, etc and lots of parents don't realizase this or don't want to but its been shown that after a certain age peers have a GREATER influence that parents have on their children. In my daughter's private school most children are from parents who are professionals (architects, doctors, engineers, business, etc) and we are actually friends with many of the parents of my daughter's peers outside of school, academic level is obviously higher, teacher-parent communication is 100% and when ever you want anytime, even the principal (even the founders of the school are friends actually), you know what is going on real-time and teachers cannot do what they want, etc
We are often in the US and we have friends there, I think you have a bit of a prejudice regarding the youth there and the education. Not everyone is taking drugs or drinking, there are some good kids there and I met some of them.
Of course Europe is socially more secure and probably safer in every day life but you need to see the drawbacks as well.
I think you have a idolized sense of it since you are only there for vacation, frequently but for vacation, when you actually live there its different. I guess every place is different vacation vs living there.
Did I mention what driving a sportscar is like in Florida?... lets just say I'd be driving a Prius if I were in Florida and taking Prozac just so I don't kill myself 
I really enjoyed some nice rides with a friend who knows where to drive to. There are so many nice roads out there if you know your way around.
Only thing I would miss are the mountain roads I enjoy so much.
Also, in Florida, I could drive a cabriolet all year long... 
Me and my wife love heat and the beaches, my wife is also a watersports (swimming, waterski, wake boarding, etc.) addict, I can barely get her out of the water when we are there. We hate the mountains (well, not really but we take not much pleasure in vacationing there...) and we do not like quiet places. Actually, once the kids move out (could take some while
), we plan to sell the house and get a nice condo or penthouse somewhere in or near the city. We're not much of nature people, we enjoy modern architecture and a vibrant city life. The older we get, the stronger the urge becomes to actually live in a place like Miami. For some people, this life is stress, for us it is pure relaxation, as weird as this may sound.
You are getting older, my grandfather actually retired to Ft. Lauderdale
just joking
its all about personal tastes, yours seems to match a busy Miami beachfront area from what you describe, maybe when your kids go to college would be an easier time to take the big step over the atlantic 
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⇒ Carlos - Porsche 991 Carrera GTS