Malder Welcome to the herd.
I was in pretty much the same "boat" as you just over a year ago, and bought a 14, and a few months later sold it and got the 18. Sailing a Hobie Cat is really not hard. Like with all things, to do it well, and competitively well, is of course an entirely different story.
To take the family out on the lake on the 18 sounds great, that's what I do, when I can get them all to come along. Getaway is another good choice.
I think you basically already summed up the main points to look for. Holes, cracks, leaks, rusty cables, blocks that are seized up, improperly stored sails getting moldy, that is basically it. A good solid older boat is better than a rotten newer one for sure.
When I bought my 18 I actually found it here on the Hobiecat forum, bought it from another forum member. That was actually a comforting thing, reading older posts from the seller, and developing trust. In fact the seller was nice enough to take me to a lake near his house, showed me how to set up the boat and took us out sailing to test and show us. Five star member, Rojoyinc, thanks.
So, buy from a reputable seller, or dealer, and inspect the boat thoroughly, enjoy your Hobie.
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