There are all shades of sailing skill out there, but if you can't singlehand a PocketShip in stock configuration, you can't singlehand anything. Now now---I don't mean to be arch, but the boat heaves-to nicely for hoisting sails, and once underway it's just a tiller, mainsheet, and jib sheet, all within reach of the helm. Personally, I'm ALWAYS singlehanding PocketShip, even if there are four people aboard---it's just easier than barking orders. As I've described on this bulletin board, I have often set the spinnaker solo, including in whitecaps. (Admittedly that's not for punters---I've gotten the spinnaker wet a couple of times doing that stunt.)
Yes, having a simple tiller clutch would make singlehanding easier sometimes. Like this one:
I haven't gotten around to installing mine, though. Another thing that would definitely be nice is "jiffy reefing," a clever collection of blocks and lines that allow you to pull in a reef with much less fooling around.
But gosh, when I built PocketShip the intention was to sail it solo to the Bahamas! I'd still do it, on a good weather report, safely and happily.
For my thoughts on coastal cruising in PocketShip, here's a thread from a few years back:
viewtopic.php?f=3&t=380&start=0Good time to reprise my "Seaworthiness" definition!
Seaworthy. Adjective. In a boat or ship, the condition of being crewed by sailors competent to know the limitations of the boat and themselves, notwithstanding any claims by the designer or builder.