We have a 19' ft trailer-sailor and still love her to bits. Easy to tow anywhere, and it's mainly in a slip a 10 min walk from the house
26 to 21 ft is a big jump down in terms of interior
size and livability. So if the bulk of your sailing involves overnighting, cruising and/or lots of people... it's not a great move. On the other hand, if like us you daysail 90% of the time, and just do the odd weekend out, a smaller boat might be tolerable.
Looking at pictures of a San Juan 26... If it was me I'd keep her, no question.
Here's a thought - store the San Juan at the coast, either in the water
or on land close to a good ramp
. You'd save the wear and expense of the long tow. For sailing closer to home, you might consider buying
daysailor or mini cruiser, which, if you're handy, can be picked up for cheap
We push our 19' boat with an older 5HP Suzuki and it's plenty strong enough, even in current
or against wind
. So a 9.8 hp outboard
is a little bit overkill and heavy for a 21' boat, I think.