Game Keeps on crashing cant figure out why. A window pops up say instruction blah blah must terminate program. Then the game server reloads using the autoreload script that I have enabled.

We also Website, Forums and will be running QB on this server. Plus I notice a bit more lag now ever since I switched from CS.com to my dedi server. Any reason for that?

One last thing whats a good software for ping boosting. I wanna load it into my dedi server to get better pings.

Running Counter-Strike Source
Dedicated Server Windows 2003
Intel Xeon CPU 3040 @ 1.87 GHZ
1 GB of Ram

(Should I upgrade to a better server?)

Make a print_plugin from rcon and paste it here so we can see what you are running.