***New to the sport: Hobie 16
***Have sailed a few years and have lots of friends that want to ride: Hobie 18mag
***Want a fast single-handed boat: Nacra 5.2
***Want to class race: Hobie 16
***Want to cruise: Hobie 18mag

I have had all three of these boats. The Hobie 18mag is a war-horse. Load it up and head out into the big wind and you will have an excellent time! The Hobie 16 is a simple, old boat. If you like to race and keep things simple, Hobie 16 is the way to go. The Nacra 5.2 is like a knife. Same level of complexity as a TheMightyHobie18, just 100lb lighter. Excellent boat for single-handing. Aftermarket sails can really improve performace. Just not that much deck space for two people.

Pitchpoling.... The H16 is easily the king of pitching. You have to be careful on any boat though. I haven't pitch poled hard enough to dump the TheMightyHobie18 or N5.2. I don't think it is important enough to worry about in the your buying process.