What we've seen on the West River is that the Taipan is an awesome choice. Those things are like Swiss Army Knives when it comes to finding a configuration that fits how you want to sail on any given day - 2-up, uni, solo, kite/no kite, etc.

They seem to do very well at the rating game as well.

But here's another idea - instead of getting rid of his current 20 footer, maybe he can consider a set of sails with reduced sail area, enough to make the boat easier to handle with one person. When he has crew, use the regular sails, when single handing, use the reduced area set. Since he's considering going Portsmouth anyway, a rating to use should be a matter of adding the corrections.

Something to ponder...