I think the whole idea of making a "run" or relocating your boat between two spots, is different than how "most" cruisers actually use their boats.
Perhaps I am missing something here but, this is my take being surrounded by cruisers every day and listening to their cruising plans as they deal with the changes of the season. I will admit to being different, having met a girl in La Paz and now making my home here, but I am on the dock every day, and all of my friends are cruisers. I am fully ingrained in the cruiser community.
Instead of thinking of this seasonal migration as destination A and destination B, with not much in between, most of the folks migrating annually think of it more as a movement to chase good weather with no actual destination in mind.
There are literally hundreds of boats doing this every year.
Here's how it works.
In the spring as the weather warms they start leaving the Sea of Cortez, heading north. They pick their weather windows and make their way North to Ensenada. This is the hardest part of the trip because there are almost no services, and the weather is always in your face, the fabled Baja Bash.
Once they hit Ensenada they tend to spread out. Some stay in Ensenada for the summer, relaxing or getting their boats worked on, but most seem to continue north, but at a leisurely pace. They are enjoying the great weather the Pacific Coast of America offers.
As summer progresses they, like all migratory animals they are watching for the change in the climate. Some make it all the way to Alaska, most do not go that far. Remember they are on their boats full time as a lifestyle. They are chasing good weather. Most do not like rain very much. Nobody likes rain and cold.
As fall approaches these same cruisers make a decision to turn around. There is no specific place, it just depends on where they are, when they sense a change in the weather is coming.
Then they head south, at the same leisurely pace, gathering in southern California, and Ensenada for the end of hurricane season, and their upcoming migration further South.
November 1 starts the migration into the warm waters of Mexico, where they again spread out. Some go south, some explore the Sea of Cortez, some call the popular ports in Mexico home for the winter.
Then as the hot weather of summer approaches the process repeats.
The problem we have here on TF is that much of the advice we get comes from folks that have been making boat deliveries up and down the coast, for somtimes decades. Their advice is spot on, when you think of life from their prospective as delivery captains. The challenge is that people actually cruising as a lifestyle are not delivery captains, and they are not in a hurry. They have zero reason to leave a nice comfortable port except the internal migration drive many creatures of the sea experience, driving their migrations.