Well I left the pitboss running overnight as a test (with no one on it, I hadn't gone on it at all), when I got up this morning (well, around noon

) it had already crashed, as expected. I ran it as an internet server, so there may have been people would tried to connect from the in-game browser (along with all the other games there), but wouldn't know the password. The last change to the log files was made at 4.15am, the file is network-2056_2-2-2006_0-49-19.txt
Contents are as follows:
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[33513.781] DBG: HOSTING a MULTIPLAYER, NEW, INTERNET game!
[33514.812] DBG: Adding active connection-level player info for NetID 0
[33516.218] DBG: Adding NetID 0 to Portal!
[33518.218] DBG: Got NetworkReady from NetID 0
[33518.234] WRN: Not responding to NetID 0 NetworkReady (state == INIT_SENT_READY)
[33518.234] DBG: Checking if we're connect complete! PeersReady=yes :: AlreadyComplete=no
[33518.234] DBG: Got our last outstanding network ready message! Sending Version Verification! (m_bConnectComplete=true)
[33518.718] DBG: Got Verify Version message from NetID 0!
[33518.718] DBG: Sending Pitboss NetID to NetID 0
[33519.218] DBG: Received pitboss info message from NetID 0
[33523.046] DBG: Got MapScriptAck from NetID 0!
[33523.062] DBG: Got MapScriptAck from NetID 0!
[33525.156] DBG: Sending sync start message everyone
[33525.171] DBG: Got a sync start from NetID 0
[45866.578] ERR: We were disconnected from the matchmaking server - Reason: Disconnected
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I'm now going to try it as a Direct IP server to see if that makes any difference.