Would need ammo boxes for demos though.
Nuh-uh. Just put in one of those global resupply plugins.
What I'd like to see? Not sure. Maybe a night with surf maps, cause that's the only real TF2 related thing I'm actually good at as of right now.
EDIT: More frequent gaming nights.

When I'm bored I fire up my own server. FFA Randomizer, friendly fire on. Turns out, you get new stuff when you get killed by your own team, so it works awesome.
Just need a map that spawns everyone in a FFA config so you can't spawnkill your own team, or obedient players who won't kill their own team near the vicinity of the spawn area.