Ed -
I would never consider moving this (not-so-big and well-equipped) vessel by water for any serious distance (of which this trip qualifies). Now, this next statement may cause a bit of consternation but, if it was me, I’d have a pro do the move. I realize that you, Ed, are an experienced trucker (and sailor) but you are going to pick up an unfamiliar vessel with an unfamiliar trailer (in, I’d imagine, an unfamiliar place where folks spend American dollars - yikes !!!).
I will assume that everything will be fine but we all know how these things will go. You need somewhat more time, money and patience than you have budgeted for.
You haven’t left yet (I don’t think). You now own a trailer which is very handy and you could spend all kinds of time down the road working out how you would use it to move your new boat. A trailer is very handy, once you’ve got it all figured out.
But, for this very first move, I’d still be looking at a recommended, insured pro. Ideally, you fly down there around pickup time and work with the driver for a few days. This headache of “the first move” will only happen once. but, this way, it’ll happen right, guaranteed.
Bottom line - I do not know of another sailboat owner who had bought a trailer and driven a fair distance to pick up his/her new boat. I’ve only heard of professional moves on land or well-planned and crewed moves on water. There must be good reasons why.
I will not accuse you of being “penny-wise and pound-foolish”. That is rude and over the top and, honestly, not deserved. It’s completely understandable why many folks, just like you, would come up with this idea. In a perfect world, given these variables and realities, there’s every chance that it will all go well. But, there’s also every chance that you may have some real problems and, since I have a feeling that you are not 35 years old (any more), you do NOT need the stress and worries.
Frankly, I’d re-consider this plan.
Ernie A. in Toronto