Since you come from my boat's homeland I have to wonder if you are looking at a couple Nauticats. Since my NC 331 is so drastically different from my last 2 boats which were Catalina Sloops and all the previous ones also I can't really give you an A - B comparison. I do like the extra options the 3rd sail gives me though. If it's an extra breezy day ..... or it's going to be later.... which is usually the case on Narragansett Bay I won't even bother with the Main since the furling genoa is easy to deal with and the small mizzen to balance things off is also easy to deal with. I even shrunk my Mizzen a bit to add the Bimini so there really isn't much driving power there....... BUT... way back there it acts like a 2nd rudder so it does accomplish the balancing act fairly well if it's driving at all.
As for your question about 'doing it again' I'd say (after hitting the lottery) and I was moving up to the 38-42 Nauticat range I would move away from the "Traditional Motor Sailors" (like mine) and go with the "Pilothouse Sailboat" Nauticat line most being SS designed and Much Better Sailers. And if I had option (of course I'd have the option since I just hit the lottery
) of the of Sloop or Ketch I would stick with the Ketch.