Ok! I'll spare you the entire story, but...
Drove up on Tuesday, and looked at it in Canmore, AB. It looked like I expected it to look, and the guy wouldn't let me leave without showing me that everything worked. And he fed me dinner and a beer
I drove as far as Calgary that night, did the Walmart parking lot thing, then put it in storage outside of Lethbridge and drove to the border.
I asked at the border, to make sure I knew exactly what to expect when I did bring it across, and after some confusion I got good news. They only go by year, not month/day. But at first he said that meant I'd have to wait until 2017!!! After double checking, he said yes, they go by year, but this year was 25 years old, so I could actually bring it across the border today.
So...I drove back to Lethbridge, hooked it up, back to the border, and no problems. They didn't even come outside to look at it.
I have little doubt that on a different day with different people, I may not have been allowed to bring it across. Quite a bit of confusion and different requirements, depending on which officer I talked to. But it worked it out.
I got it home last night, and now just need to register/title it.
It pulled pretty well, though I don't have enough experience with trailers to know. It'll need some kind of anti-sway setup for me to be really comfortable, and obviously I need a brake controller.
I won't say I "didn't even notice it was there", but it wasn't exactly like pulling a parachute, either. I knew it was there, but my truck did just fine with it.