The best airports, from the standpoint of interesting flying and interesting scenery on arrival, are

KCLW is a fine airport. But it has a few quirks. Check the NOTAM about night ops. With it getting darker earlier that may be a problem. Not super easy to get a rental car there either. FWIW the last time I flew down there I went in at St. Pete and parked at Sheltair. 1st class place. Treated me all right in my little bug smasher. Pulled the rental car right up to me and did a first class tie down job. The cost was cheap too. I think I paid like $10/day to park on their ramp. But that might be wrong and a little high, the cost are little fuzzy since it has been a couple of years. I just remember not being annoyed at the overnight charge.
KCLW is a fine airport. But it has a few quirks. adventure tours usa Check the NOTAM about night ops. With it getting darker adventure tours usa earlier that may be a problem. Not super easy to get a rental car there either. FWIW the last time I flew down there I went in at St. Pete and parked at Sheltair. 1st class place. Treated me all right in my little bug smasher. Pulled the rental car right up to me and did a first class tie down job. The cost was cheap too. I think I paid like $10/day to park on their ramp. But that might be wrong and a little high, the cost are little fuzzy since it has been a couple of years. I just remember not being annoyed at the overnight charge.
I'd focus on two things: the person adventure tours usa who is picking you up and the weather. CLW is a short, one-strip airport so consider the conditions if you plan to use it. It is not particularly easy to find (not just in the air but on the ground) without the ubiquitous Tom-Tom or Garmin in the car. Sheltair at PIE is first-rate, as Scott mentions, and they have the govt. gas contract for Tampa Bay so you're likely to see some military hardware on their ramp, plus have the fun of watching the USCG ops - biggest USCG air base in the nation, not that it poses a problem when landing or departing. But Sheltair is also hard to find by car, being tucked away on the back (north) side of the field, so get directions for your pick-up to use as even a GPS probably won't do the job. Multiple adventure tours usa long runways minimize VFR weather as a factor.
The easiest commute adventure tours usa to/from your arrival point (to Oldsmar) by your pick-up is the Jet Center FBO at TPA. It's always been a high-end operation in the past (I have no current experience there) and I would probably not consider it in any event. Class B airports are not really for us.
The best airports, from the standpoint of interesting adventure tours usa flying adventure tours usa and interesting scenery on arrival, are Peter O. Knight (TPF) and St. Pete Municipal (SPG). Sadly, neither is convenient to Oldsmar....but then, it isn't you that's driving.