I can answer a little about the sloop vs cutter. I had a 39ft cutter at one time and many sloops.
Advantage of the cutter over sloop that I found was mainly more flexibility in what sails you could rig for different wind. ie. You've got 3 sails and the different sizes of each. And it looked great under full sail. Disadvantage - more work tacking, hoisting and furling! I prefer the sloop :-)
Back when I had a Mottle 33 a friend had a ketch with slightly less water line length. He was always slightly faster than us

Very annoying until he ran aground one day on a mud bar and we missed it and sailed past