Paul, yes, tacking is a bit of a chore, particularly if the yankee is large, as ours is. There isn’t much room between the stays for the sail to pass through, as you know. When we are going to tack, we roll up some of the yankee first, then it goes through fine. If we are short-tacking to windward, I just leave the yankee about 35% furled. The staysail, as you know, is on a boom, and takes care of itself; our staysail is not roller-furling, btw. Between the partial yankee and the staysail, we have decent power for beating.
I love the flexibility of the cutter rig. We have three reef points in the main, and with the yankee variably furlable, there are lots of combos. I even put one traditional reef in the staysail. If we had to, we could deal with a ton of wind with triple-reefed main, reefed staysail, and no yankee.
Yes, the CD 31 was built at the end of Cape Dory’s existence, ’82 to ‘85. They built 89 of them. A sweet boat, and rugged.
http://www.capedory.org/specs/cd31.htm
Interestingly, the 32 (they only built 11 of them) has a deck-stepped mast. But the 31 has a keel-stepped mast, like the 33, 36 and larger models.
The 28 and 30 are also excellent boats. On your 28, was your jib on a boom? The boomed jib would be excellent for single-handing. There are lots of CDs up here, and most 28s I see still have the boom and a 100% jib. But some folks have no doubt gone with a bigger genny, and therefore removed the jib boom.