Running a server completely headless is fine as long as the server boots and remote access is available (via ssh, rdp, vnc or similar). I have a HP mediasmart EX490 server which has no VGA output (though it is possible to get a VGA/PS2 connection with a debug cable). These are some tips for running the EX490 completely headless with Ubuntu.
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Home Networking, Networking, Ubuntu, Webserver