I've dug a hole to drop the wheels in on the street side of the trailer. Sometimes it is necessary! Yes I have plenty of boards for leveling, but I'de rather not have to pack a parachute for my wife and kids for the last step from the trailer! If the campground can't level the site for me I'll do it for free!
I however would not dig to use my tote. but to make a week or weekend easier to get in and out I'll do it. The only time i didn't my wife twisted an ankle stepping off the steps. I had close to a foot of boards on the curb side tires and way to many under the tongue jack!
Becareful where you walk no matter where you are! And yes I fill the spot back in, the next guy will thank me for the loose dirt!