I had to install Debian because, as it turns out, it isn't a good idea to first install squeeze, install a ton of packages and then try and migrate to Wheezy. So I did that, and now TF2 is up and running. Apparently, I hadn't seen the little note on AppDB which said to turn off MOTD mods in the Advanced Settings dialog in TF, so I did that and now it all works fine, if a bit slow. Thanks for the help and support guys :)