I guess I'm the guy that hit the needle in the haystack... I bought my boat a little over 3 years ago (found on C-list)- 1984 with about 500 hours on the engine (Merc 228 (Chevy 305)). Almost everything on the boat was original. Paid slightly less than $5K. She was and continues to be a freshwater only boat- stored inside.
All systems had been maintained well. Sea trialed with my father-in-law who was a boater for 30+ years and a big DIY guy.
Only real trouble I had was with the shift/throttle control- which was on the list to replace as soon as I bought the boat.
That being said, I have probably put $2-3K into preventive maintenance and upgrades over the past 3 seasons (New control, new VHF and antenna, dual battery set-up, new depth-sounder / GPS, full tune-up, oil changes, drive lube changes, upper drive seal, belts, water pump, trailer tires & brakes, trailer lighting, winch, etc).
My view- I had an expert help me choose this boat, and it paid off. The boat is safe and reliable, and I knew I would be putting money into it to upgrade / maintain that. I've used this boat to learn all the basics and am confident in my abilities to maintain her. Even with the upfront and annual costs, I can entertain my family all summer for a fraction of the cost of expensive vacations and outings. I wouldn't trade our boating experiences for anything!
I think there are still diamonds in the rough to be had out there, but they are not easy to find. Even if you do find a newer, better vessel- you need to budget to maintain it. I have friends with boats that are 20 years newer than mine, and my boat is in better condition (though the color scheme may leave something to be desired
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-Andrew
1984 Four Winns 225 Sundowner
5.0L Mercruiser, Alpha 1