Yeah I'm a 2000 server user too (Advanced Server actually), works nicely. I've got cable, so I didn't mind doing the updates until Microsoft seemed to limit the bandwidth for Windows Updates to cable Internet user. But it works well for use as a DNS server a Web Server, and ok as an FTP server. I personally use Bulletproof for FTP, more options. Security wise, I never really had a problem. Like I said the FTP server never really gave me much options, but I think that was just in design. Everything else worked fine for what I needed it to.

I've tried using Linux (Redhat, etc) as a server, but I always had problems trying to network my Windows boxes to them. Plus I started having issues with trying to figure out how to work the damn thing. < I'm not THAT skilled with unix/linux yet either >

So that's my oppinion on your question.