Linux

This is a really good way of saying it!

I'll give concrete examples. With Arch:

• you either upgrade frequently, or risk a painful upgrade. I find I can reliably go a month between upgrades, usually with no problems, which doesn't seem too bad... unless you're used to upgrading once a year.
• frequent upgrades mean you often have to reboot, because the kernel changes frequently. This means rebooting at least once a month, sometimes more frequently.
• the previous is exacerbated because Arch expects that, if you "update" your repos metadata, you must upgrade all packages. You can install new packages if you don't update, but you can't selectively upgrade individual packages - at least, it's considered unsupported and a bad practice (pacman -Sy <package> is bad). So if you want to upgrade to Inkscape to a new version, you may find yourself having to install a new kernel which might force a reboot.
• you can pin packages, but it's not exactly a user friendly process. To do this, you have to edit a file in /etc, and then keep track; and if you do want to upgrade a pinned package it's a bit of a PITA. You can easily get yourself into a bad state by pinning packages, and it's easy to forget about pinned packages.
• if you simply don't update the repos metadata, software frequently becomes uninstallable because upstream sources disappear. This happens to me far more frequently than I'd expect; like, in a matter of days between updates.
• Arch's package config (/etc) management is primitive. It just dumps new versions of config files in the filesystem, and it's up to you to notice, find, and merge them. There are third party tools to help, but they're basically dev-level diff/merge tools. You have to realize this is going on, go find a tool, install it; and because of the previous points, it means if you want to upgrade Inkscape, you may find yourself being forced to merge a grub config.
• news sucks. Arch regularly (more frequently than other distros) pushes out breaking changes - things that will screw up your system. You are warned about these not when you try to upgrade, but only in Arch news, which you're expected to go and read any time you install software. This means that upgrading Inkscape can break your system, if you don't first go and read the Arch news; and Arch news readers are not installed by default, so you have to manually install and remember to run this every time you run pacman. You may be lucky, but it you aren't and it bites you, you'll be told by the Arch community it's your own dammed fault for not checking news first.

Despite all of these terrible, fixable aspects of Arch, I run it everywhere. Why? Because, unlike Debian, I don't have to wait two years to get package updates, because the Arch package repository is simply vast and comprehensive, and because if you get in the habit of navigating the Arch maintenance minefield, it is the least breaky of distros, and the easiest to fix if it does get broken. I've had Debian installs get so fucked up, the package db so broken, that the only fix is to re-install. I've had Arch get borked, but never to an unrecoverable state.