I have a server thats primarily used for SRCDS, I host a few Team Fortress 2 servers on it and I would much prefer a ssh-like (more so the no-gui part) for something like this, mostly because I can't navigate with my phone on VNC very well and also because there really is no need for a gui in this situation. I sort of want to make the switch but I am unsure, because my server 2003 is very fast and If I do need to reboot, it can reboot in under 30 seconds to desktop. Should I switch?
No, what warren suggested is sound advice. Cygwin would be the way to go. There's no reason to go through the pain of setting everything up again on a new operating system unless you have other reasons such as: wanting to learn linux, wanting to use linux to lower your per-month server costs (assuming you don't own the Win2003 server license outright) etc.