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So am I crazy, are they holding their value for a decade, or is it a really bad time to shop?
Welcome!
I can't say much about Horizons holding their value, but I will say that we paid $6,400 for our '99 H180 w/ 130 OB back in 2011. Based on your searches, did mine make money?
Normally, shopping for boats to buy in the Spring is a seller's market. Prices are usually higher because the season in N. America is about to begin right now. Better to buy during the late fall or winter (if things aren't completely frozen over - not sure how winters are in KY). We bought our boat in mid-April, btw.
With current conditions (COVID crap), that could give you an edge on pricing. Not much stuff selling if people can't go anywhere.
FWIW, don't rule out a FW with an outboard if you run across one. Maintenance is a lot easier than an I/O and they're pretty easy to work on yourself.