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Lived in South Tampa (Hyde Park and Beach Park specifically) and have lived in Thornton Park and Winter Park and would choose Orlando over tampa. Biggest reason is that Orlando is a more transient community and more diverse. Orlando metro communities are much more welcoming than their counterparts in Tampa. I love living in Winter park. I have zero desire to go back to tampa. Lived in both places with young kids too and there was no shortage of things to do in Orlando and we immediately felt welcome. Tampa, not so much.
I lived in Orlando for a year and a half and been to Tampa Bay and Orlando metro for 1-3 week vacations since 1977. I have gotten to know both areas well. I absolutely love that whole I-4 corridor from Orlando to Tampa Bay, to visit AND to live.
As far as CITY, I personally like Tampa better. This is not saying Orlando isn't good. Just that I think Tampa offers more on the whole.
As far as METRO, Tampa. A little more so here. The things that Pinellas County has gives it a boost.
I found both metros to be very family friendly (our kids were in elementary/junior high at the time), friendly in general (felt very welcomed in both and made awesome friends in both), unlimited things to do, good economies, and pretty affordable (especially in the Lakeland/Tampa stretch of I-4). With Tampa and Orlando being so close and having close access to each other's offernings, it makes it that much better.
This is just a general overview and my own personal experience. You'll need to do your own research to determine what meets your detailed needs and wants and to what degree each area meets them. To me, you can't lose with either. Good luck in your search.
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