I'm piggybacking off some other ideas I've seen and tentatively adding this here.
I think that to fix some of the backlash over the 100 tokens thing, it could be beneficial to add a system where the number of tokens you have equals the chance at a WW when you “roll”.
If you have 20 tokens, you have a 20% chance at getting a WW and an 80% chance at losing it all. The only guarantee would be if you have 100, like how it is now.
It could be getting close to gambling territory, but I think it'd be more satisfying than “you get nothing until you have 100."