Muscle memory has a lot to do with it.
After more than 20 or so years on 8" trucks, in 2017 when I went from 139s to 144s on an 8.12 deck, a lot of how I skated changed just a little bit, as the wider truck meant you had to land more square on for nose or tail slides, but now I am on 149s or bigger boards, it doesn't matter so much, or I am more used to it.
Others I know still ride the 139s on 8, 8.12 and even 8.25 boards because anything other than that feels weird and their tricks don't work as that is how they have skated for 20 or so years.
Most of us had been on about the 139 size for a long time, so it was a big change to the 144s and lots of people didn't like it, or just went back to 139 / 8" trucks on their boards.
Going back to older or even 80s style / fish shaped decks, truck size didn't come into it half as much, but there were still specific sizes that you lined up on your deck to check first, usually wheels sticking out at the back, but the wider front of the board and wide tail meant you never really caught your foot on the back wheels either, as you were used to how wide the whole setup was.
Part of skating back then was riding things that others passed on to you, or you just skated what you had until the absolute last dying moment of whatever it was, so nothing got changed out anywhere near as regularly as things do now, be it for lack of money, knowledge of product or any other reason.