Losing matches is hard-coded because I was too lazy to finish the subsystem which determines that. I guess it's also subtle political commentary? It's slated for the next release or maybe the one after that. Skill is actually more like "how good of a pro wrestler are you," instead of "how likely are you to win." Rivalries and titles are on the roadmap (which I should post soon).
It's funny you should mention going on the road, previous versions of Rassler were explicitly doing this (each match was in a different town) but it didn't feel like it meant anything in the state it was in, so I ditched it until I had time to make it meaningful. Heading down the road is definitely central to the pro wrestler experience I want to provide.
Gear change is a great idea. That might go in the next release, it'll help with the "endgame" a lot.
Thanks for the thoughtful feedback.