I'd focus on two things: the person 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 long runways minimize VFR weather as a factor.
The easiest commute 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 flying 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.
Jack