"Yes, but its done based on server, not by game, servers should be assigned to games, not games assigned to servers"
Tomato, tomatoe.
Either way has same effect.
"You can have something set as installed by default, but not something that is installed afterwards by default, the files must already be there"
I keep all my mod install files on a single web server, taking away the need to transfer files to each gameserver. So yes, it works that way for me.
"winpcap isn't, unless its changed recently"
I have installed 3-4 remotes recently and never did winpcap by hand on them, bandwidth stats works; I also recall seeing it being installed during installation.