I've always wanted to play this game (and probably will, now that it's free), but the longer I wait, the higher the barrier to entry seems to be. I feel as though I will be completely lost and confused when I first boot up TF2.
I browsed the "Uber Update" thread, for example, and was stunned to see all the new weapons released solely in this single update. They all have damage modifiers, crit modifiers, mobility restrictions, and so on an so forth, and that's not even including weapons released in previous updates. Also, there's the whole deal with item crafting (I seriously have no idea what this is or how you do it) and crates (likewise). I would have absolutely no idea where to begin or know which weapon/item combinations are the most useful.
The things that originally attracted me to TF2 were the artstyle and apparent simplicity, the latter of which seems to have been lost in the years since its release. It's fantastic for fans looking for new ways to play the game, but no-so-great for people like me now intimidated by the vast amounts of weapons and items added to the player inventory.