An interesting question... I do not use a checklist when loading up to head out to dark skies.. This how it works for me.
At home in San Diego, I have most of room we call the "scope room." I have two Dobs in San Diego, three in the high desert. They rarely travel unless we are going somewhere in the motor home. They are generally assembled but if they are disassembled, everything is together. I have two chairs in the high desert, one at home, they don't travel.
My refractors each have a case and are ready to go, complete with diagonal and their own finder. I have a main eyepiece case, that has a complete set of eyepieces from the 28mm UWA to the 3.5 mm Nagler, the Paracorr 2, my deep sky filters, a Barlow. I have a tool box with all my telescope tools, including my collimation tools, spare batteries for everything, wrenches, screwdrivers, etc. My additional eyepieces are organized as sets, they are always in their case when not in use. I have bag with binoculars and miscellaneous stuff. I have a leather camera bag, my SQM and SQM-L are here plus some overflow eyepieces. I have a case with nuts and bolts, larger tools, extra Teflon, holes saws.. The cases are all on a large storage shelf.
Some stuff always goes. Some stuff I decide on when I am ready to load. Before I begin loading, I put everything on the floor in the middle of the room, the refractor(s) I am taking, the tripods, the eyepieces, the finder(s) etc etc. Once it's there, I check it out, I look at the shelves to see if I have forgotten anything. And then I begin loading the truck.
In the back of the truck is a large cardboard box, 24" x 36" and probably 18 inches tall. When not in use, it folds flat. When I start loading, I begin the same way each time. First are the tripods. I wrap them individually in blankets. Next I load the box starting with the main eyepiece case and the parts case. Between them go the tool box with the collimation tools. It is always the same and always just like that. If I have just that plus a finder, I am set. I have everything I really need. This is consistency is a check list of sorts.
Next come the binos bag, the leather camera bag, the finder(s), refractor(s) and additional eyepiece cases...
When I am done loading, I look around the scope room to see if I have forgotten anything.
Not having to move my Dobs and chairs back and forth simplifies things. The organized loading of the truck means I will have what I need and anything I forget, it won't be something critical.
Jon