The more I think about it, the more I agree with Kayin (I think it was Kayin): Just give everyone all the new "usable" items outright, and make people earn (or "earn") the hats. I mean, if people want to cheat or lame their way into the cosmetic changes... well, whatever gets 'em through the night, I guess. Strictly speaking there's not a lot of harm in that.
I get the premise behind earning new items, and I even like it in theory, but in practice it's kind of a mess. For example: I would never have known that I actually really like Sniper if I hadn't randomly gotten Jarate once. Some weeks later, quite bored and somehow on a team with no Snipers, decided that I may as well try it out. Turned out to be pretty cool, so I stuck with it for awhile, unlocking the Huntsman through achievements, where upon it all made sense. The Sniper was for me.
Note that the entire sequence of events starts with the word "random". I'm glad for the existence of random drops at all, but my point is that this kind of discovery shouldn't be at the behest of an rng or earning achievements. If I had never got that jar of piss or had to earn it through achievements, I never would have at all since at that point I had long since written off Sniper as my least favorite class.
Am I making any sense? I feel a twinge incoherent. My base point is that if they're going to put all this hard work into making and balancing these new toys they should just let us play with them. I'm still waiting on scoring an Eyelander drop so maybe I can find out that I don't actually hate/suck at Demoman, because I sure as heck ain't gonna earn it through achievements unless I go a-whorin'.