There is a lot of useful info on this forum (and others). Search around and you'll probably find more information than you ever dreamed you could need. The most important thing to look out for, especially in older boats, is what are known as "soft spots." These are localized areas of delamination in the hulls. They are basically an indicator that the hull has reached the end of its useful life. Small areas can be repaired by injecting epoxy, but it's kind of a blind process with no real definite time span for how long the repair will last. Larger areas more or less can not be repaired (or at least are not worth the time and expense of attempting to repair). To identify soft spots, press firmly on the surface of the hull. There should be little to no noticeable deflection. If you feel significant movement or hear crunching, the hulls are delaminated. The most important place to check on a H16 is right in front of the front pylons.
Otherwise, you really just want to give a close inspection to the big ticket items (mast, boom, sails, hulls, crossbars, rudders, trampoline & trailer). Look for damage such as dents, corrosion, tears, cracks, etc. Expect to replace wear items like lines, halyards, and standing rigging. The nice thing about Hobies is that for the most part, a visual inspection will tell you just about everything you need to know about the boat.
There have also been a lot of upgrades to the design of the H16 over the years, so the newer the boat you can buy, the more user friendly and better performing it will be. The construction quality has also improved over the years. So if you can find a boat from the 1990's or newer, you should be pretty well off. The boats from the '70s and '80s are really starting to get up there in age and are a lot more likely to have "issues."
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