Larger boat
That's why we moved up to the 32 from a 26' Islander, but it's not all roses and cherries. My 200lb mooring is not quite adequate, and surveys, haul outs, and transient slips are more expensive now. The room on the inside is about the same, and the hull speed is similar. The 5' draft in the upper bay is a little challenging as well. Not to mention, the work involved in fixing an affordable 32.
I'm making most of the same updates to the 32. I'm getting ready to put in a newer Atomic 4, I've disconnected the AC Shore power until I can update it. Plus installed the new bulkhead over the winter. I still need to repaint the hull and deck, and reseal the deck fittings.
I'd love to make it down to Tangier, in prep for the loop, but it will be a few years even for that. The youngest of my crew is 3, and usually is good for about 3 hours of sailing per day. If we can organize a day in the fall between Rock Hall and Havre de Grace, I might be able to make it depending on my work schedule. I'm not sure of any events other than downrigging weekend in Chestertown, MD, but that's pretty far up the Chester. At least there are plenty of anchorages nearby.
Dean