Windows 2000 Server is convenient and easy to get going if you have a Windows network and just want to share the odd file here and there with one or two Macs.

Unfortunately, it makes a nasty replacement for a proper AppleShare server in a predominately Mac environment. Microsoft intended Services For Macintosh to ease the transition from Mac to Windows and as such, had no motivation to make Windows act as a fast file server for Mac clients.

For starters, it's single threaded. This becomes painfully obvious when a Mac user attempts to search a shared drive with lots of files on it: all other Mac clients virtually stop until the server completes the search operation (yuk). In addition, it doesn't understand encapsulated IP in Mac packets... and then you still have to find a Windows compatible LocalTalk card or an ethernet to localtalk router/bridge.

I'm not sure that there is a universal solution, but I get on reasonably well using a FreeBSD box with Netatalk for Macs + Samba for Windows machines. A dedicated Ethernet to LocalTalk router that understands TCP/IP encapsulation takes care of my LocalTalk only Macs.

[Edit: and yes, Netatalk can be messy and a pain in the bum to get going if you've never used it before]