Trailers aren't
cheap. And they regularly break, which gets really expensive fast. The cheaper the deal on craigslist, the more likely to break. So if you want to move the
boat once, hiring the transport is probably a good idea.
I have a
C&C mega 30, with a lifting
keel and a tabernacle stepped
mast. Designed to float on / off the trailer and have the mast raised / lowered by one or two people with the
equipment on the boat. A low estimate I got for a new trailer was $4k. And most of the trailer places want to charge another 1-2 K because it's a sailboat, so figure $5k minimum. (and the $4k was estimate for 24' trailer because my
rudder is transom hung and can be removed, and doesn't need any support from the trailer on the last 4 or so feet of the boat)
Used trailers seem few and far between. And would probably require some modification to fit, and possibly major
work to roadworthy. Researching trailers on some other
forums and you'll find many people who double there boat workload cause the trailer is that much more
work. On any used trailer chance are the brakes don't work, especially if someone put it in
salt water. And it's really hard to test them without putting your boat on the trailer, unloaded the brakes shouldn't be noticeable.
When I first towed my boat home with a dodge 1 ton (D3500 with cummins deisel, and rear disk brakes) I wondered how people towed loads like this with 1/2 ton trucks. Later I discovered the brakes didn't work, while replacing both axles that had cracked (rust half through) trying to back up in a tight spot leaving the boat launch's parking lot (pushing the trailer almost sideways backing the truck around it).
So, while my boat is out in front of my house waiting for that touch up
paint, I am spending all my time fixing the trailer under it.