I have twins and a teen ager. You'll be fine, there are tons of things to do here for both. My twins are 4, I also have a 7 year old.
Florida is full of every kind of "folk". You're not going to have a big problem with diversity here. We have our intolerant types of course as all areas do but if you stay urban in your choices you're not going to run into any issues.
Having said that, this isn't Dallas/Houston/Austin/ATL/SanFran/Chitown/DC where your alternative lifestyles are concentrated in fun, colorful and eclectic areas of the city. Everyone seems to be sprinkled about. Once you've met a few kindred souls here they can fill you in. There's a wonderful alternative dance bar in downtown Dunedin and some wonderful places on Central Ave. in St. Pete.
Unfortunately we're kind of the poster child for intolerance right now with our transgender City Manager in Largo getting "outed" then "ousted" and in my opinion it's an absolute discrace. We'll start another rant about that later!
Alternative hang outs are largely in South Tampa and Channelside, Ybor City (north of downtown tampa) and down around downtown St. Pete. Also pockets on the beaches (which will be popular with the teenager - mine spends a lot of time there.) There are some locally published papers to get you a flavor for what to do and how to meet. Creative Loafing Creative Loafing Tampa
used to be the Weekly Planet. Also Tampa Area - Hillsborough, Pinellas, and Pasco County
(http://eisnerfeldman.com/About-The-Tampa-Area/ - broken link) has an About the Tampa Area section with a map of the three counties and a discription with links of to information about the different areas of town. And a resource section that contains info about services around the counties Eisner, Feldman & Grant
(http://eisnerfeldman.com/Florida/ - broken link)
Sports and entertainment are pretty much centrally located in downtown Tampa. There are of course other wonderful venues around town but most big name performers / concerts are either at the Tampa Bay Performing Arts Center, the St. Pete Times Forum (which is where the hockey team plays) or the Ford Ampitheater (which is on the East side of town a little out of the way - it's an outdoor venu where most musical acts perform
Ok, the hospitals that you've mentioned... do you already have jobs there? There are LOTS of other hospitals here and medical professionals are in high demand. I don't nknow anything about what you do specifically but there's a nice concentration of hospitals in downtown St. Pete too. Just a thought. I'll go with what you've already written.
A good general website about the area is TBO Tampa Bay Online. Breaking News, weather, sports and things to do
Tampa Memorial Hosp. is located in the S. Tampa area and isn't that far away from Town N Country hospital but the S. Tampa area is far more expensive. You won't find any trouble renting in either location and the spaces will be nicer in S. Tampa and it's a walking community. Even the Old Hyde Park shopping center is being rennovated with a new book store soon! The teenager will be happy in either place probably but will be closer to night life in S. Tampa.
Hillsborough has a school choice plan. Here's their website
Hillsborough County Public Schools (HCPS)
And the site of the state's school evaluator site so you can compare schools. Florida School Indicators Report
enter "Schools" then when it gives you a pick list you can choose all highschools and get a rating. You need to speak with the district about your choice issues. You can't enroll until you have a verifyable address (lease or utility bill in your name)
Ok, Brandon and Riverview - unless you want to spend all your time in the car I would say you wouldn't be real interested in those areas. The crosstown expressway will get you to TMH pretty quick but your companion will have it much rougher getting to Town and Country (45 min on a good day each way). Plus you'll drive to get everywhere else you might want to go. Housing is newer and affordable there but it's pretty sub-urban. It does have a nice mall and there's lots of new construction there so I won't talk you totally out of it but it's sort of de-void of style and personality.
The Town and Country area has some crime spots and most of the housing is smaller/older so you might be happier going a little north to the Citrus Park area or a little East to Carrollwood.
A good site to check before you rent/buy is the Sexual Preditors list FDLE Florida Sexual Offenders and Predators
Crime stats are here: Florida Statistical Analysis Center (FSAC)
A great site to check out any zip code you'd like more details on is FreeDemographics
And, to get an idea of how far your dollars will go here compared to where you are is a cost of living calculator Moderator cut: link removed
just enter your salary and then choose the two cities to compare various expense categories.
My teenager spends time at the beach, Mall (the two best of which are close to S. Tampa as well) Busch Gardens and going to the movies with friends. Your twins depending on their age and gender will enjoy the zoo, aquarium and the children's programming that comes to town at the performing arts center (we don't have a Children's Museum yet but it's planned - just needs some funding!)
I wouldn't recommend areas of Pasco County for the same reasons I don't think you'll like Brandon or Riverview - far away - you'll give up too much of your time in the car. The veteran's expressway or I 75 are jammed in morning commute. There is newer, larger housing there and the schools are good so you might still find it's worth the commute to you.
I hope this is helpful to you. Good luck in your move!