There is one advantage to short shoes.
I'm sure you can get used to ducking with the lower headroom, but the taller trailer leaves you with more options.
Let's say you want to go to the races and potentially use the trailer for some sort of gathering spot.
Maybe you want to use the trailer to help your friends move for the umpteenth time.
It might happen, . .that you need to use the trailer to do a small overhaul while up in the northwoods.
Maybe, you actually like the finish on the top of your helmet.
No matter how often you remember to duck going into the shorter trailer, you will still have occasions when you forget.