The Paceship looks good for your needs.
I too, love the classic looking boats, but the ones you're looking at are rather narrow in the beam. A 27' LOA, 8' beam boat is going to be cramped on those full-family outings, and may turn the family off quickly.
A 26-28 foot beamy boat, or a 30 footer with a moderate beam should be easily single-handed by you, and comfortably fill the requirement of the occasional, full-family outings.
I do have a spot in my heart for the Catalina 30, but it's quite beamy, displaces 10,200lbs and you might find it a chore to single-hand often. This would reduce the amount of use you get out of it, and we don't want that.
Also, the choice isn't "one or the other". Pearson 30's were designed as "cruiser/racers", or "family racers" if you will. They are comfy, reasonably equipped, and a spirited sail. Displaces 8800 lbs. The S2 8.6 would meet the same criteria, I think, and displaces 7600lbs.
The Tartan 30 is another great boat, but I think it begins to push your "easy single handing" criteria. The beam is in between the Cat 30 and P-30.
Any of these boats would comfortably sleep 4 for several days, 6 for a few days, and can be single handed without too much hassle. I just won a single-handed race in my Pearson 30, and I don't even have it optimized with all the lines run aft to the cockpit, or an auto pilot.
I call it "racing my living room".