Been to Outback Bowl twice. IMO, best overall experience in Tampa, compared to San Antonio, Orlando and Miami.
Jon is right. Charter is more experience, but you have no worries.
We planned a trip the last Outback, and we had to stay at 2 different hotels in a 4-day period, which may not sound like much of a hassle, but there were 4 of us traveling, and the La Quinta double beds were quite small, and we ended up paying for another room.
The Tampa Marriott was awesome. Then, the Syracuse basketball team was staying in that hotel. I didn't see Boeheim, but saw the trainers and some players.
Parking near Ybor City on New Year's Eve can be tricky.
I"m a person who likes to plan everything on my own, so I'll be planning it myself.