I was considering purchase of a Cape Dory 25 (1975) with trailer for $5700. The trailer is rusty and the boat needs a new coat of ablative bottom paint, the teak needs to be resanded and refinished, and there are some cracks on the deck which don't look deep. I could not find soft spots on the deck. Is this a reasonable price?
I see dozens of CD25s on the market. They were about 1000 made and they don't seem as popular as the smaller or larger CDs. They are a little big for a day sailor a little small for a family coastal cruiser. There should be no problem finding several for sale nearby on the east coast or great lakes. Look to see what else (CD25 and otherwise) is on the market to determine what is reasonable.
Most boats of this size and vintage need paint and brightwork. You will pay a premium for one that does not. That premium might be well worth it.
Do you WANT a trailer? Is the trailer SOUND and what you are looking for?
I see a huge advantage of being able to haul the boat out myself when a major storm is coming, store/work on it in my own yard, and move it hundreds of miles to go explore a new sailing area.
However, finding a GOOD used trailer for a CD25 is hard. I looked an almost nice Greenwich 24 (same hull) a few weeks ago that had the hull deformed over time by the homebuilt trailer that it came on. Sellers are asking $1k+ for a rusty piece of junk you have to use a crane/lift to load and I wouldn't risk driving at more than 20mph. A good new launchable trailer for a CD25 will cost about $5700 by itself.
Do you have a 3/4 ton or bigger truck to pull this boat and trailer?
Why do you think you need a 3/4 ton+ truck to pull a 4000lb boat on a 1500lb trailer? I personally think 4LO and a high tide are important if you launching/retrieving at a ramp. But it doesn't take a large powerful truck to pull 5500lbs up a ramp or along the highway.