Hi Jeff -

Personal opinion, with just you and a 5yo, either of the 6.0s might be a bit much to handle. They're heavy and even more prone to flipping when solo than the 5.8 that you mention. I wouldn't write off the Hobie boats too quick - there will be lots in your area, many good used boats, and people who can help you along as you and your son grow into a boat. The Nacra 5.0 is certainly a fine boat if you can find one, but it can be flipped, too - I'd recommend you stay in the 17-foot and smaller range for your search. A Hobie 17 or a Nacra 5.5 is about as big a boat As I'd feel comfortable taking my swim-ready pre-schooler on in anything more than six or eight knots.

Don't limit your search to the glass boats, either - get your feet wet with a Wave. Super simple to rig and will sail quite well for you.

Happy shopping - let us know what you wind up getting and post some pics of your youth sailor! <img src="http://www.catsailor.com/forums/images/graemlins/grin.gif" alt="" />