what sort of living arrangement do you want to have? Rent/buy? Condo, house? Single guy? GF/wife....kids???
Cheapest and easiest lifestyle is to rent or buy a condo in a mid-rise (less than 8 stories). HOA fees will cover property insurance, since many major insurance providers don't even underwrite homeowner's insurance policies now if you're within 5-miles of the Gulf.
Understandably, low-maintenance living comes at a sacrifice of storage space...which is why you may need to get a storage unit.
If you rent/buy a house, landscaping and home repair is expensive and a pain in the ass. You won't want to mow a lawn when it's 95* and 100% humidity for months on end. Plus, most of the lawns need a sprinkler system, and your water bill will be ridic.
All that being said I agree that Clearwater is the nicer community south of the area. However, check out Edison College/St. Pete Beach area. Nice, older condo communities you could live in and be right next to the water. I highly encourage you to BE AS CLOSE TO THE GULF AS POSSIBLE, because FL is not as nice if you're further inland...and as mentioned you simply won't go to the beach as often. I knew people in Naples that went YEARS without going to the beach...boggled my mind since you can't drive west without eventually going into the Gulf...
Let us know what's up down there for you!