For around $350 you can get a G-force, Kingpin (Original, icon sucked), Disco, Full-Tilt, Transformer, S-6 (plain S-6, not F or X), Pop, Space Cadet (if you're a good roller), Chronic, All-star original, ZG, or Vibe. $250 is baseline kayak that floats, $450 is something with miles left and not too old, but $350 gets you anything from a cracked Alien to an OK Project... choose wisely.
$450 Mint-condition S-6 Full-tilt Chronic Crazy 88 or Vibe, Orbit Fish, 07 All-star, Project, Bliss Stick RAD,
$500+: Like new RAD, Great shape Project or 07 All-star Orbit Fish, 2010 All-star, cracked Rockstar or Project X.
Personally, I would go for a beat-up newer design over a mint Kingpin anyday - even just frontsurfing a small wave there's just a world of difference between our original All-star and our newest All-star or Rockstar.
Here on the top wave of Rock Island where we used to spin and muscle a roundhouse we can now get clean airblunts, back pan-ams, and grind down the green section - the new hulls are just that much better.
Happy choosing -
Team Jackson Kayak