My vote is on the 16, I was in the same "boat"
that you are in last summer, I went with the 16 and I'm happy with it. I mostly sail solo but friends will want to go, and you'll get the itch to go crazy and get wild, you'll want a crew for that for sure. It's nice to have the option for solo or crew sailing or even taking 3 or 4 out for a slow cruise. You don't have that in the 14. Besides at a little over 200 I was a little heavy for the 14 solo, let alone with anyone else.
I'm in Michigan and we have a few H16 fleets around here, most of the guys that I talk to are super cool and are willing to help show you the ropes/lines, they'll go out with you and show you how to work your rig, on a 14 they'll have to tell you on land then you have to go out and actually remember what they said
The 16 is by far more popular and for a reason.
Good luck and happy sailing.
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Cesar (Cez) S.
Hobie 16 (had a few)
Nacra 5.2 "Hull Yeah"
Vectorworks XJ - A class (not named yet)
West Michigan (Grand Rapids/Holland Area)
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