I've never run out of room updating Debian, installing other misc crap on Debian, yes, yes I have run out of room. To be fair I have 50GB partitioned off for OS on a 250GB 2.5". The other is not my Home partition, but a NTFS partition with all my files on it.
Not plain Debian, but Ubuntu I have, and frequently. The reason being that it sets up way to damn small of a /boot partition, and then does an absolutely horrible job of cleaning up anything from routine updates. So every so often you have to run an apt-get autoremove and autoclean. Course, that doesn't really clean up /boot 90% of the time, so you have to go in there and manually figure out what kernel related packages to purge. If you either a)don't have a specific /boot partition or b) have a very large one, you'll end up with gigs and gigs of unnecessary update files hanging around.
Hard to say.
It is a lot harder to hack a *nix system. Not that it cant be done. But there has never been a widespread hack, virus etc on linux ever like is common on Windows.
I think you are thinking back to the original XP days, that hasn't been common since Vista (or really SP2 in XP). Mainly because Microsoft throws their software into sandbox testers (I forget the term right now) and finds a lot vulnerabilities not easily discovered by the original coders. A lot of servers on the Internet run on Linux, and if you think that all these data breaches are just from companies running Windows servers you'd be mistaken. It's not hard at all to setup a Linux box improperly and leave yourself wide open.
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To me Linux's place is on the server. Run it with or without a GUI and either deal with community support or get behind Redhat which has been doing quite a lot of work to get it more compatible and easy to just 'use'. On the desktop....that's another story. I've used Linux for years as a primary on my laptop in college, and then primary on my desktop at work. Every single time something about it just pisses me off. Something doesn't work, something breaks, it has annoying incompatibilities, or the most stupid error messages 'Ubuntu has detected a problem!' and I rarely figure out what they mean. I had a pretty standard setup, i7, 16gb ram, Intel video, and a SSD. Doing an update, which happens every damn day, frequently meant that if I rebooted the video wouldn't load and it would throw me into recovery mode or the command line. Nothing I did would ever fix that, so I just stopped rebooting until necessary. Oh, not to forget that Ubuntu only has Trim support on a few select SSDs...really? It's 2014, they've been out for a long time now. Or the GUI, which subsystem has needed to be rebuilt (and yet hasn't) for a decade now.
I got so fed up with the stupid little crap that Linux would keep throwing at me I switched back to Windows 8.1 for my primary at work. Thus far, absolutely 0 problems, everything works like it should, and I can get work done without dealing with the problems of my PC first. Plus, it's been faster than Linux was.
On the server I get using the command line for a lot of things, I still find it annoying but it works. On the desktop, I despise having to drop into command line regularly just to do basic things. Why they still haven't figured out how to easily install things is beyond me (yes yes, rpm's are nice buy only on fedora based, and don't even bother with Ubuntu's 'software center' it only has a few random things in it), and even after years of experience with it the file structure still confuses me. I've rarely an idea of where things install what.
Basically, Linux just ends up annoying me. It's free and all, which I guess you get what you pay for. With Windows at least I know it will work, and I've paid Microsoft for that ability and the support it brings as well.