Windows

Things to Hate About Windows

No Secure Shell (SSH) client or server in base system
Although there is a CLI (cmd.exe) its complete lack of capabilities and sophistication renders it virtually useless
Inability to mount, burn, create or otherwise manipulate ISO or other disk images

Hopelessly disorganized file system makes properly maintaining a Windows installation an exercise in futility
Changing IPv4 settings while an Ethernet interface physically has a connection causes Windows to hang for several minutes while it pretends the task given to it is in some way complicated. (At least in XP, haven't confirmed this on Vista)
Product Activation - Users of Windows are all filthy software pirates until proven otherwise, nice!
The inner workings of the system are completely obscured from the end user with no option to make them visible. System hangs on boot? Just keep guessing what the problem is. No verbose booting is possible.