We ended the day with some winch issues. We had been winching the Tiger backward up the ramp into the trailer. But the system had had a lot of difficulties and needed plenty of engineering. Here you see a photo of the aftermath of me giving up on the crappy Harbor Freight winch. The trailer's floor, while easy to clean (which is great!), offers crappy traction, and its ramp is steeply angled, so getting a top-heavy bike like Tiger in and out is more of an adventure than I'd prefer. The system has evolved through a few Soviet-era-appropriate modifications to make it work.
For now the solution is probably to ride the Tiger in, and back it out, and hope for the best. Does my bike insurance cover falling off a ramp? Maybe.