If you buy a clean, well cared for boat, it will only lose value over time. If you buy a dirty boat that needs a little work but is essentially sound, you can put in some sweat equity and have a decent boat that you may be able to turn around later without much loss of value. The problem is that in your budget, you can only find old boats. The number of older boats that have been really well cared for isn't that great.
S/V Legacy, Catalina 400 MkII, Hull #328
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