Shipped two big boats across the country now. We had to take the flybridge off the last one but happily the marinas did a great job on both ends (Coeymans on the Hudson, and Lewis & Clark in South Dakota) but we were lucky. Cost about $3000 on each end for breakdown, loading, unloading, and reassembly on a 37 footer (that wasn't the trucking itself, just the costs on each end). The fact that Mainship built the thing to be taken off relatively easily helped a lot, could have been far, far more complicated and expensive. We got such an incredible price on the boat that it was worth it, but that's the key -- it's an overall cost calculation to see if buying a boat in the "wrong" place and shipping it home makes sense. My advice echoes a lot of others on threads like this, don't fall in love with one boat in the wrong place. Be patient grasshopper and you'll snag a really good deal eventually.
Well, here, perfect example coincidentally -- I'm hunting for a small, very inexpensive classic-style sailboat to keep around the CT River for summer weekends on LI Sound when we go out to visit my mother. Kenner Privateers from the late 60's, early 70's really caught my eye about six or eight months ago. There are some out there with asking prices of $14,000, $25,000. I want to pay a small fraction of that so I've just been patient, waiting in the weeds. Found one in Michigan for $5K, but then I'd have to move it all the way to CT. Just found one on Ebay in beautiful shape with an opening bid of $1,000. We'll see how the auction goes, but my point is, patience pays off.
(Hey, don't anybody scoop that auction on eBay, I want that Kenner, back off! I should keep my mouth shut, now it'll probably go for 52 million bucks and I'll have to keep looking.)