My dad had a 21-foot cabin cruiser that we took out on the Chesapeake Bay as much as possible. It was about the biggest boat he could get that he could still put on a trailer. He liked the idea of being able to go different places with the boat.
I watched and listened to my dad driving around in lots of different situations, and I got a pretty good sense of what to look out for, and what kinds of stupid behavior made life difficult for people pulling a trailer.
There’s a lot more to it than this, but the most fundamental thing is that people pulling a trailer have to deal with a lot more momentum, so they start and stop more slowly.
It’s been a few years since I’ve hauled a boat. My boat died and I mostly use kayaks these days. I just mount them on the roof. But we just drove down to Nashville with a trailer full of decorations and supplies for a wedding, and I got a fresh reminder of how un-courteous and just plain stupid most drivers are.