We're in Riverview, lower-middle class rising. 25 minutes to downtown Tampa, 10 minutes to Apollo Beach. $200k will get you a brand new 2100-2400sq' single-family home in a cookie-cutter subdivision. There are new developments less than 5 minutes from my front door.
Brand new is nice; houses built to modern hurricane codes make insurers happy.
Downtown Tampa has condos, if that's appealing. Great views, city-like conveniences.
15 minutes east of 33578 will get you a few acres of pastureland and 1500sq' and position you very close to the Hillsborough river and great mountainbiking. (yes, seriously).
New Tampa, 30 minutes north of me, in northern Hillsborough county, is upper middle class. Bruce B. Downs is the major artery in New Tampa, google maps will let you browse the area.
Sarasota / Bradenton might work for you also; it's charming and has character. Smaller than Tampa but not as rural as Lakeland / Winter Haven.
I suggest staying near the coast. The further east you go the more stagnant it feels and you're just that much further from good sailing.
St. Petersburg and Clearwater are on the other side of the Bay. I drive through it often but cannot speak to the housing situation. It doesn't seem to be in "growth mode" like Riverview or New Tampa.
Hope that helps. Happy to help with specifics as you need.
Dad lives in Louisville. I'm from Lake Cumberland area. Spent time in Lexington and still have family dotted all along from Hyden to Somerset. I suspect I know how you feel.