I think there's something to be said about the "comparing to others". I don't know if milestones truly achieves that as it is right now where I've anecdotally seen more comparisons of how much TPE each person got rather with maybe side mentions of what categories they achieved, but not one that makes me think "I want to compare our season's performance". Most importantly of all, it's just an echo effect on the season you and your team had. As mentioned if you're on a strong one or a weak one, that strongly dictates how much milestones you've achieved. Especially if you've had a bit of bad luck, getting 1 or none just feels bad because there's largely nothing that the user could have done to change that, short of forcing his coach to make him get into a fight once a season or something.

I've thought maybe team based milestones being the top 5 scorer on your team or top 5 in hits or something that could be more intrateam recognition. Same problem above applies in that you can't really help it if you're played 10 minutes on the 3rd pair in your rookie season

What about career based milestones? Lots of logistical questions to answer with this in terms of combining both old and new players. I'm not a fan because this one more inherently pokes at the issues with milestones and that's how we track/judge them. Goals and assists make sense, but then for defensive players who lack stats on FHM's side to determine their effectiveness beyond number counting stats come back to one of the fundamental issues with milestones as they are right now.