Neither of these are good options.
That said, the exception is a browser, where I would prefer to use the upstream version for security reasons.
Honestly, anything that a developer has pushed. Sometimes I want an SVN build of DOSBox or need a bleeding edge feature of some tool I use all the time. On Windows, this is simply a matter of downloading a binary, but by and large Linux software doesn't work that way. Distros expect that you will use whatever version of a package they have seen fit to grace you with, or you compile from source like it is 1975.
It is not unreasonable or unrealistic to ask for a stable platform upon which one can run bleeding edge applications, yet this remains painful on Linux Desktop.
For the few cases were you need bleeding edge you can just download and run it just like on Windows. For most applications bleeding edge is really not necessary and you can just normally install via package manager.
Though I don't think the situation is that bleak. Any popular application where user have a reasonable interest in having the latest version should have some way to ship it on Linux?
Thinking about what I personally use, blender just has a tarball, no trouble, VS Codium, Godot, Unity, Love2d all have AppImages, the IntelliJ IDEs can be installed via snap. Browsers are handled by package manager. Most of my dev stuff is running on docker anyway.
Yes, it is a bit of a mess with all the different ways to ship binaries but I can't think of something I am painfully missing. I don't care about having the newest version for most apps though so maybe I am more easily pleased.
Why would an employee that wasn't part of IT procurement ever be thinking about that? If you're telling me that it's impossible to hire a single person for procurement who can figure out whether your machines will run on the OS your organization has chosen, I'm going to insist that's not true.
> I’ve never had a Linux box that didn’t require me to open a terminal to fix something after a while.
I'm going to make the guess that you never run a stable distribution for your own personal desktop, like Debian stable, for example. For some reason, most individuals pretend to need a bleeding edge desktop. Organizations don't. Debian Stable is as fragile as a mountain.