OK, I'll take a stab. First, there is no changes to flserver (including the window title string) after the patch is installed. Good to see you installed it on the SERVER and not on the CLIENTS.
He connects but you time out? Never heard of a timing out issue which makes me think it is something not related to FL. Like is either of you getting dynamically allocated IP addresses? If say his address changes after 15 mins and you connect to the server through the Internet using the global server, then it may take a while for the global server to update with the new IP address. I thought though it takes less time than that. Could be other things like an ISP not wanting you to play games, upsetting ports and such. Try changing the port on the server to another and see if that does anything. FYI flserver uses only one port of the normal spread (2302-2304) that FL says is used through DirectPlay. Changing to another port is fine and is the only one that should be port forwarded through your firewall.
Of course the above paragraph is not very useful if when you restart flserver you don't also restart the server 'puter itself. That tells me it wouldn't be a dynamically allocated IP address thing but maybe some esoteric bug with FL or DirectX on either 'puter. Ensure you have all drivers like DirectX up to date. You have no idea how many problems there have been which have been solved by a correct and good DirectX (re)install.
I had a hell of a time getting Win2k to work for me. 3 days and it wouldn't work but it took me 3 hrs to set up and run WinXPPro. I have heard it mentioned around that SP4 will work with FL. You have all the latest service packs for Win2k?
Good luck!
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Earendil
SysAdmin of Boston Freelancer server
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