Thanks for the great advice folks! Reading some responses I think I need to clarify what I REALLY am trying to find out.
I am not looking for an ever-dry sailboat, I don't want to stick a mast on a pontoon boat or anything like that. I am pretty sure that the keel boats @SHNOOL suggested are nice but not what I am looking for. Firstly I would prefer to be able to beach the boat, but more importantly I want to be able to grow into a faster mode of sailing, even if that means splashing the boat a few times along the way.
My main concern is that I don't want to buy a boat that - as I heard about Hobie 16s and especially 14s - are all too easy to mishandle even if you are not trying to run them down to the wire. For instance, I heard that a Hobie 16 can pitchpole if it catches a wave even at moderate speed. Or, some boats may be very tricky to handle in certain situations (tack or go upwind or what not - sorry, too dumb to really know).
Those are the concerns. If I overstate them (e.g. a Hobie 16 won't pitchpole unless you are flying a hull at 15+ knots), or if the Buccaneer is notoriously shifty on a jibe, or if either of them takes forever to rig, that's what I would like to know.
Of the suggestions above, I think a Prindle 16 would be a much better choice for me than a Hobie 16 - I am a 210 lbs. tub-o-lard, so a Hobie 16 might simply not carry me. Unless I can find one, I will probably pick out of the available three (Buccaneer, AMF Sidewinder, Hobie 16), unless I hear something that makes them completely unacceptable. Right now I am leaning towards the Buccaneer because I hear it is among the more forgiving performance dinghies, and it is still in production so parts should be available much easier than for the AMF Sidewinder.
Thanks again for all the suggestions, I am sure I will be coming back for help on how to not flip whatever I buy quite so often
Oh, and @CaribDream: I am in Rochester, NY - I think that still counts as upstate unless for you Long Islanders civilization ends 100 miles up the Hudson