both servers will launch and after about 30 secs the first .191 server will timeout in HLSW. The 2nd .192 server will stay up and play normally (and be visible in server browser).
We tried to at least keep an eye on whether our servers were up and running through HLSW. We noticed they repeatedly timed out. Checked the console errors on the main server box (Windows 2003 64bit) and noted continuous error messages. Turned out that the problem was HLSW accessing the servers.
Stopped using HLSW and the errors stopped immediately.