Well, I have to fettle Linux servers for a living (Spacecraft construction isn't all fun and games.
), so I'm more than happy to use a command line. In fact, I prefer fettling that to having to fettle the Windows Registry, which is sometimes required if a Windows box is really playing silly buggers.
At least on a Linux box, if ssmtp isn't working, I know there's a good chance that the comments in the /etc/ssmtp.conf file will provide some guidance, whereas a similar problem with a Windows box will leave me Googling through MS KB articles trying to find the right key buried somewhere in the HKEY_LOCAL_MACHINE hive ...
Windows tends to do a better job of providing a GUI interface to something, and generally is more consistent with that, but both of them fail big time once the GUI runs out, and you have to start digging around in the internals.
At least with Linux, if I really have to, I can resort to looking at the source code, although generally if you've got this deep into it, then you're probably on a hiding to nothing unless you've spent the last five years working on that project. With some programs, like Samba, even the log files are so tortuously complicated that working out what isn't working is a challenge in itself, even before you then have to work out what the solution is.
Clearly Linux has done a lot better in the server world, because the sort of people who need to run this stuff, often prefer the relative openness of the Linux community vs the downright secretiveness sometimes of MS. The desktop world is getting better, but of course tweaking the way that configuration GUIs are programmed in an app isn't that much fun, so there's not as much drive for people to sort out some of these problems. Things like consistency in interfaces is hard to enforce when the nature of the Open Source community is very much about the freedom to do whatever you like. Enforcement if very much the antithesis of that.