Keep in mind that Hobie 14s really sail best with only one person on board. You can sail with two people, but once the total crew weight gets above about 250 lbs, the handling and performance will really suffer. If the boat is a standard 14 (no "turbo" jib), then you will have a little bit of a learning curve as far as tacking goes as these are among the most difficult boats to tack.
By far the most important thing to check for is soft spots on the sides of the hulls and the decks. Press on the hulls all around, if the surface deflects easily, it means the fiberglass structure has delaminated and the boat should not be sailed. Small soft areas (about a foot in diameter) can be repaired with epoxy, but if the soft areas are much larger, you should probably pass on the boat. The most common area for soft spots is on the deck, directly in front of the front crossbar.
Otherwise, check everything over really well, focusing on the mast, boom, trampoline, and sails. These are the expensive parts to replace. I recommend bringing a copy of the Hobie catalogue with you when you look at the boat so you will easily know the replacement cost for any missing or broken parts.
Otherwise, good luck with the boat and welcome to the sport.
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