Andrew, I could see Jen helping you load the car up on the trailer to get you to go out to an event. Haha. No question in my mind of the real reasons why you haven't been able to run.
LOL she's done it before, when I was still very new to trailering the car solo and wanted an extra pair of eyes outside the car, or needed a guide to line up the trailer & hitch. Now in the course of an hour I can have the trailer hitched, car on the trailer and tied down, and all my gear loaded up solo. In fact a lot of times having someone help me now just wastes time and they get in the way. I've got my "system" down pretty well lol