Winseer:
The only bad habit I ever picked up with coupling up, was sometimes forgetting to jump out of the tractor before going under, to check the trailer brake was on…
More than once I’ve gone under, lifted it up with the suspension as I do, only to find I start pushing the whole thing back a foot before realising the red and blue buttons are both pushed in…

I never go under when anything or anyone is behind a trailer though, so no harm done.
I’ve yet come across that thankfully, all our trailers are either backed onto a raised loading bay or we don’t drop them except for parking them up at the weekend in which case if we didn’t put the brake on we’d be picking them out of a swamp 
My procedure for dropping is back onto the bay parking brakes on, wind the legs down collect & stow the number plate, unclip the dog-clip & pull the king pin release, uncouple the suzis, draw forward a wee bit drop the unit suspension and ease out from under the trailer.
Hooking up is back up to the trailer, drop the suspension once the 5th wheel is just under the trailer raise the suspension so the unit is taking the weight of the trailer (makes it a lot easier to wind the legs up too) and back on to engage the king pin, check the position of the release lever and fit the dog-clip then walk under and check the locking bar on my way to raise the legs and release the brakes, back to the unit and put the suspension into ‘travel’ connect the suzis and fit the number plate.
The problems come in a normal single decker unit and the trailer was dropped by an old type decker unit and the trailer is up in the sky, have had to back partially under and wind the trailer down on the low gear until the weight is on the 5th wheel, no big deal but if you’re not looking for that then it’s easy to under-run the king pin & crunch the side deflecters, which I did the first time this happened
but only a little as I back on fairly gently.
Given winseers comment I may have to revise my routine, i.e. check the trailer brake before I back under