Personally I use iftop on my Minecraft server. i'm by no means an expert user but it serves it purpose to me.
edit--just noticed gawdnfreeman's post. Woops.
The small image is iStat Menus, and the larger terminal is iftop.
I don't run Windows at all, but ntop looks like it might be similar. Also iftop might be compilable under cygwin. I don't know what kind of access cygwin has to the network hardware.
tcptrack is nice, iftop is better :) Available in most repos as well.
I've also found that having a few of your own cli initiated status scripts to check on this and that can help you unplug from a problem, and all the typing and screen scrutinizing looks terribly productive.