Each individual has his own objectives and for some trucking the boat is the right answer. You can't be dogmatic. As I explained my plan started with sailing all the way home - "trip of a lifetime" stuff. Circumstances changed on the way and the decision taken to abort and truck the boat home. Better to pay the money, have the boat back home than leave it in Spain until I could organise things to complete the sea journey - which would have been effectively a year later unless I paid a full time delivery crew which would have cost almost the same. I would then not had the pleasure of being on board which was a big part of planning to sail it home. Trucking was the only rational decision and 2 weeks later boat was sitting on my mooring in Poole ready to sail.But the point of owning a cruising yacht is to sail it to different places?
Yacht ownership is really not about the cheapest way of gettign your boat back to its home pontoon.
I completely agree about the time and weather, the trip is not a small commitment, it's likely not going to fit into a typical 2 weeks off work.
Boats are a black hole for time as well as money.
The OP hopefully now has an idea of the pros and cons of the two alternatives and make his own decision.