Heck yeah, I would also like the ability to choose where the pins go so you can neatly organize them on your blazer. You could also have medals, badges and other neat things.

We would need a new tab in the watch with each challenge and as we complete them they tick off and possibly even have a progress bar with milestones

I absolutely love this idea

I really like this idea, having a sash as mocha said would also be very cool. It could have a couple slots for equipping said pins. Might also be neat to be able to equip one pin where your cheer icon would be.

There could be a small Icon in the profile menu for easy equipping.

Also some concept art:

What if there was a sash that gets updated whenever you complete an action, or get an amount of kills with a certain weapon.