How to get active contracts

Free accounts can't get hat drops. As I recall, you upgraded to a Premium account (and gave @badp the Professor Speks... jealous), though.

There are 3 drop timers:

1. Items. Standard is 6-8 a week, assuming you play at least 6 hours a week. Note: To my knowledge, paints and tags are part of this timer, but they have a lower chance of dropping. Immediately following an update, Valve tends to raise the drop rate for those items. Right now, you're guaranteed to get 1 Uber-update weapon a week minimum.
2. Crates. Standard is around one a week (sometimes two), assuming you play at least 6 hours a week.
3. Hats/Misc. Standard is one every 1-6 months, assuming you play at least 6 hours a week.

The length of time that counts towards your next drop is limited to (iirc) 6 hours per week, but if you don't play for a week, the next week will be limited to 12 hours.

Hat drop rates vary wildly. I've had an 8 month stretch with no hat drops before, but more recently, I've been getting a hat every 1-2 months.

Side Note: The hat drop rate is bugged during the rare Double Drop rate week. While the first hat drops at the normal rate, the second uses a much, much shorter timer (the crate timer?). So, it's not unusual to get two hat drops during a double drop rate week.

_restart

or

quit

From my small experience of running tf2 servers I remember that you would need to reboot the server for it to kick off updates. Assuming you use the standard srcds_run Linux script, it should restart within 10 seconds. If you are using a server provider and you are still hitting a brick wall talk to them :).