I did this myself in 1999; shipped my Pearson 30 from Florida to Long Beach, CA rather than buy a different boat in CA. Here's the equation that lead me to that decision. The 19-yr-old boat had an estimated value of $20,000. Selling through a brokerage could mean 10% commission on the selling price. Then, purchase of a replacement boat in CA, the sales tax would be I think about 8.5%. So, say the replacement is $5,000 more for one in comparable condition. We have $2,000 + $2,125 = $4,125 transaction costs.
The initial shipping estimate/quote I got was around $6,000, BUT if I was willing to wait for a double load to form (i.e., two boats on one trailer), then it would be half that amount. So that's what I did. However, it cost me about a grand on each end to decommission and then recommission the boat in Long Beach. Out of pocket the total shipping cost came to some change over $5,000, which in the world of boating costs is basically a wash against the transaction cost of selling and then buying, etc.
The intangibles. My P-30 was in very good condition. The available boats I saw while scoping out the situation in CA were not in as good condition. The variety of choices for boats is much less in CA that on the east coast. This wouldn't matter to someone looking for a Catalina to replace a Catalina. But forget it trying to find another P-30. The practical choices would be limited to Cal, Ericson, Catalina, Hunter, & Newport, plus an assortment of even older models from companies out of business such as Islander and Ranger, etc. But you would not be seeing much in the way of Morgans, Irwins, Gulfstars, Pearsons, Tartans, Sabres, and etc.
Just another FYI. I recently got a quote to ship my Bavaria 38 from Long Beach to Tacoma; it was about $8,300. Add in the decommission and recommission, and we have about $10,000 for that job @ less than half the distance you're talking about.
KG