What an Interesting Forum
I haven't been on this site for very long even tho my bio says 0005 but it's interesting to hear all those different opinions . We're all opinionated and I'm no different; but at 71, previously being a professional racing crew, and having over 50 years sailing experience, I hope no one will begrudge me mine.In the size of my current 37' cruiser a sloop has worked fine for me and I have had no problems raising the main. Whenever I removed it, say for summer storage in Mexico, I had help and it was no problem. I have cursed my 135% genoa however when I have to pack it up, roll it up, put it in a big bag and cart it below, but I've managed. The cutter rig would seem better because it has smaller headsails, has more flexibility in heavy weather, and is easier to tack going up wind, but the big jib I have reduces fairly quickly with my roller furler, and I would hate to mess with running backstays which on a cutter offshore should always be set. Additionally most of my long distance cruising has been mostly off the wind. At about 40' and up however I believe in multiple masts to break up the sail plan and make sail handling easier. Even reefing or furling a big main has its problems and the cutter rig becomes more attractive even with runners. Your staysail on those boats may very well be on a boom to make weather work even easier.How the masts are configured however is a matter of personal taste as Ketches, Yawls, Schooners, or combinations of each like Yawl Rigged Ketches, Ketch rigged Yawls, Schooner Ketches and etc.I don't like cats except around a bay because without a headsail you can't heave to or balance the rig. Unstayed masts seem ok though, but I like to have a place to fly my pennants/flags And I have been known (in my younger days) to go up to the spreaders to have a longer look. So my personal history makes me more comfortable with stayed masts. I think that if I had an unstayed mast I might have to be very careful not to over trim the jib when going to weather.All boating is a personal thing, so anything can be just right for somebody, even the very experienced.