Ok, this is the THIRD and LAST time I'm going to try to address this topic. Here's hoping I don't get booted off! The readers digest condesed version is as follows:
Bertino, I've seen a classic case of exactly what you speak of - an avid, skillful, frequent sailor of a 24' boat bought a 33' and pretty well stopped sailing.
Bilgeret, do you actually live on your boat? As in, that's your residence? If so, very cool.
More philosophy: I don't think I need any encouragement to keep my boat, rather I suspect I'd regret swapping up and would need more reasons to make the jump. I'll re-frame the original question to see if that makes it clearer. The question could be posed as "how does one manage in a large volume boat?" How do you brace yourself across a cockpit 10 ft wide? What keeps you from dragging your pencil across your chart when you slide off the navigator's seat? How do you do anything on the high side of the cabin without a hiking trapeze? Maybe the answer is that I haven't had the "luxury" of sailing on a bigger sailboat in nasty weather. Maybe the trade for more comfort in the majority of conditions outweighs occasionally feeling like a pebble inside a barrel rolling down a hill. Most of the bigger boats I know in these parts motor when the going gets tough, and that is no improvement most of the time. Sailing WITH bigger boats is a good idea though for, as Bilgeret points out, they make a fine party platform. Ok, here goes the "submit" button...
Afterthought: Speaking of head whacks, did I mention I have a retired work helmet on V. for the day the barrel starts to roll? At least it's a small diameter barrel!