Re: Shipping a new boat cross country (Canada)
This is a pretty popular boat in Minnesota, Wisconsin, and Michigan, but I sympathize with your transport problem. There's a lot of not much between you and anywhere where you're likely to find these boats. My brother-in-law lives up in Saskatoon, so I've been up your way a few times.
I'd say get a rail quote and see if that cuts the cost down, otherwise pick your road carrier and bite the bullet. Given the wear and tear + the $ involved in driving that far, I think you are right to have it shipped and then it's somebody else's problem.
I'm in MN and I looked at buying a boat in Florida and driving down. Between the fuel costs both ways and the hassle factor + the time, there was no savings in it. Unless the current owner has flawless maintainance logs that show when the bearings on the trailer have last been overhauled, now way would I go on that long of a trip without redoing them first. That's a long day project IF things go well.
One thing I WOULD ABSOLUTELY DO is contact your insurance company and make absolutely sure that you are covered even when the boat is in transport by a third party including coverage for theft. Of course the transport company should pay for damages, but you IMO you can never be too careful and having a backup insurance that will cover any losses would make me sleep better.
Good luck.
Grouse