Shipping it by truck makes the most sense in my opinion. If this was the beginning of summer, I'd say go for the adventure if you are up to it. But this time of year will put you under some pressure from the short days, blustery
weather and cold temperatures. It would be a hard
delivery and nothing more.
Since the boat will be new to you, you don't know that everything will be in shape for this type of trip. From cutlass bearings to
raw water impellers, that type of trip is hard on the boat and
motor. You may only get part of the way there and be shutdown by
equipment failure.
Motoring 10 to 12 hours a day at this time of year means that you are starting and ending in the dark. It will be cold and monotonous since you wont be able to stop anywhere interesting due to your schedule.
The expense of
shipping it would be easily offset by two hard weeks of effort driving your
new boat in the ditch. If you
work with a trucking agent, and have a flexible schedule, you may be able to get a really good deal with a truck who would be otherwise returning home empty ... or "deadheading". A trucker with a boat
trailer would rather have a boat on that
trailer than drive home empty. They will give you a good
price if you
work with a
broker.