IMHO you have a few other things to consider as well. First of, most trailerable boats use a swing keel, water ballast, or something like that to make the boat trailerable. That compromise usually has a negative affect on the boat sailing ability, or requires more maintenance, etc. For example, the Catalina 22 trailer sailor has a swing keel. The swing keel is great if you trailer sail the boat (don't leave it in the water). The swing keel is NOT recommended for extended use in salt water (the keel pendant and other components wear much faster in salt water). It also hums and bangs when sailing.
Also, most boats bigger than 22' will require a crane to step / unstep the mast. Sure you can rig up a gin pole or something else, but the mast gets real heavy and can get dangerous pretty quickly.
With a small boat, like anything designed for trailer use, and under 25', doing it yourself (with your own trailer and tow vehicle) is OK. Get bigger and I think you're better off paying the yard.
For me, the cost of having my 35' boat hauled, mast removed, transported to a 'you do it' yard, stored all winter with access to water and electric in the spring, then transported back to the water, mast stepped, and boat splashed, is about $2000.00.
I pay it without complaining.
Deep Blue C, 2002 C&C 110
Mt. Sinai, NY
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