The PHRF ratings are a good indication of relative speed differences: PHRF New England - Handicapping - Base Handicaps
According to the N.E. PHRF, the Cat 30 is 180, the Cal 29-2 is 183 and the Watkins 29 is 219, and the Pearson 10M is 135 or 141. In a race, the Watkins would be given an extra 39 seconds each mile to catch up to the faster Catalina 30. The Pearson 10M would give the Catalina 30 an extra 45 seconds per mile to catch up.
On the Chesapeake Bay in particular, even if you don't race, you do not want to have a slow boat or you will spend most of your time motoring. If you are lucky to have enough wind consistently to sail on your coastal passages, you will appreciate the greater speed over the course of much greater differences.
Cabin space is highly overrated. If you are like most folks, you will not spend that much time below decks. Sure, it is nice to be able to stand up and move around, but a little extra space may not be worth the penalty you pay in boatspeed.