Same here... I used to work down there 1998 - 2000.
I used to stay at the Courtyard on Ulmerton just in St. Pete right off I-275. It was in the center of hot spots as far as wanting to hit the coast of St. Pete/Clearwater and the downtown Tampa spots. Don't forget about Ybor City. I always had a good time down there. We used to hit Bar Tampa on Thursday nights. I saw more boobies than I can remember.
We used to eat at the Salt Rock Grill a lot.
http://www.saltrockgrill.com/ The outside deck is great. The front bar used to get a little spicy late in the evening. We ran into Hulk Hogan and the Undertaker a few times. We also used to be able to get a good cigars there and smoke on the back deck. They're located in Indian Rocks Beach in St. Pete. Tarheel's been there, so he can vouch for the place.
We used to hit Jackson's a bit as well.
http://www.jacksonsbistro.com/ Back then, I believe they were known as Jackson's Steakhouse. They're located in the Harbour Island area. Good food... Classy dames...
Back in the day, a few of the Tampa Bay Buc cheerleaders worked at the Winghouse on Ulmerton.
Don't go to the original Hooters. The few times we visited, the ladies were absolute dogs.