Pokemon has a number of community created challenge modes where you apply a certain set of restrictions to how you play, the most famous being the nuzlocke. I came up with a (new?) challenge run since the exp share in SW/SH was bumming me out a bit; I felt like I was always using the same three pokemon. Here's the rules to my challenge:
It's been fun to play, and has added a real challenge and variety to the game. Of course, I made a webapp to keep track of it all for me. Everything is stored in a github gist as a pseudo-database; you can have multiple challenge runs at once, add pokemon to your pool, give them nicknames, evolve them, select forms, etc. It keeps a record of your current random team, allows for generating a new one, filling it out if you bench a pokemon on your team.
It was mostly made for myself and is pretty specialized to this one challenge run. But if you'd like to try it all you need is a github account to log in; it will auto save and create a new gist. Check it out here.
Next: Moving to FoundryVTT