FWIW, having gone to the Outback several times, as well as snowbirding in Dunedin, FL, here are some suggestions:
1) Stay in St. Pete Beach, Treasure Island, or one of the other gulf beaches. You're leaving the midwest, why not be on a beach? I prefer VRBOs to hotels, but that's just me. I'm old and aren't out on the town every night anymore.
2) Do go the parade in Ybor City; it is fun.
3) The Columbia is a great restaurant in Ybor City. There are also a couple of other locations in the area, but I like the historic aspect of the Ybor City site.
4) For high-end seafood, Oystercatchers is great. If you are in the Tarpon Springs area, Rusty Bellies is very good and at reasonable prices. It's a Greek community, so you can find some good Greek food.
Have fun!