Having 
used WinCVS for so many moons, both personally and professionally, there’s one thing that annoys the hell out of me:
When importing new modules, the dialog that shows which files are going to be part of this module and the recommended way of importing (binary/text/unicode) , doesn’t allow you to do a multi-select and tag or toggle. Nope sir: each file extension has to be selected individually, and set (in a second pop-up box) to the required format.
I’ve seen version 1.3 to 2.0.0.2 and it’s still not right. Sure, you might just as well upload a cvswrappers file or edit it in a SSH session, and drop it in the modules’ root directory. But hey, WinCVS is supposed to make it easier. And don’t mention TortoiseCVS: it sucks big deal and is only used by developers that don’t know how to set up WinCVS, because (taadaa) it does it automatically for you!
Oh. Wait.