As a mechanic for over 50 years, it's personal preference. I winterize and clean my boat in the fall but I don't change the engine oil and filter until the spring.
Some people like to do everything in the fall so that they can just drop it in the water when the season starts. I prefer to check it all over in the spring before it goes in the water.
It's really not something to lose sleep over.
It's like which way do you hang your toilet paper, rolled up or rolled down?