UPDATE: Took the good advice (again!) and booked the later flight. This will be a 50 minute connection instead of 2 and a half hours.
A question though. Form one of the posts I gathered that CO Express comes in on a different terminal than CO. My flight into CLE (from LGA) is CO Exp, and 50 minutes later the flight to TPA is Continental. Is 50 minutes enough time to make the connection?