Originally Posted by MarkSF
I don't think you'll have any problem finding what you want. There are lots of great swing keel designs in that size range, and many are already set up for single handed sailing. Small Craft Advisor small ads are one way to go. Found this straight away :
Small Craft Advisor - West Wight Potter 19
In answer to your question about equipment, it might cost about $2k to buy a roller furler for the jib, get the jib adapted to suit, bring all the reefing lines and main halyard back to the cockpit, and buy a tiller pilot. I had lazy jacks but took them off, did more harm than good.
But there are so many smaller boats out there set up for single handed, I don't think you'll have any trouble finding one.
I agree with MarkSF on all points.
I'm sailing a 26 foot Pearson Ariel that's well behaved in the even sometimes-challenging conditions in the SF Bay and in the swells of Half Moon Bay, and yet, she's got enough sail area to do 3 knots in 6 knots of wind. It's better to be poking around a little slower than you'd like and have some stability under you.
I've sailed many times from Marina Del Rey to Catalina, and sometimes the conditions down there can be more challenging than predicted. I'd want a boat that can stand up and take more than I'd want to go out in because, inevitably, the time will come when those Santa Ana winds will come screaming through when you didn't expect them.
I have an old school hanked on jib because - it'll always come down. I've seen too many people up on their bows trying to unfoul a roller rig -- and sailing single handed -- you want to avoid ever going up to the foredeck.