Value of boats based on age, use and location

I am looking into getting my first sunfish (two, actually) and I am trying to figure out how to go about it, since I am in an unusual situation. I live in Puerto Rico and used boats are not plentiful, and so far are priced way higher than in the US. Here are my current choices to get two boats:
I can buy two 1998 sunfish from a sailing school. They come with a trailer and a dolly. Everything is very used, but completely functional. The boats have obviously been sailed a lot, but are in good...

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