Hey Danno,

As you can see, you've received a tremendous amount of advice. One question I have for the group recommending the Nacra's is price. I'm not familiar with the going rate for the N5.5, etc.

My two cents. I learned to sail on small boats like Sunfish, etc., and moved to a Hobie 16. I now have a Hobie 18 Magnum (includes wings). It also has a roller furling jib. A used TheMightyHobie18 can be had for the $2-3k range, and includes several of the attributes you ask about, and that I appreciate.

The roller furling jib is great when sailing solo, or when coming in. The wings also are great for friends and kids, and you get a bunch of weight out over the water hold the boat down before having to learn how to trap-out. The TheMightyHobie18 is also a much friendlier boat to sail, bigger hulls, greater stability in big wind or waves, and much harder to pitch-pole. Finally they're plentiful and inexpensive, and important attribute for the WAF (Wife Acceptance Factor).
Good luck.

Dan Simmons
'79 Hobie 18 Magnum - Sail 886
Mallets Bay on Lake Cahmplain, VT