Non free software is too. Especially when you start dealing with licensing. Where I work we have people assigned to licensing & other people assigned to actual install. Of course the licensing goes through a third party provider... for which we're a third party provider to our clients

ALL software does this. If it works, I might as well have let someone else do the waiting.

If it doesn't, then It requires a few hours mindlessly running around until you find some stupid flag that was set. Which I might as well leave to somebody else to do.

That this is the state of software is a pretty damn good thing, that most of it has become busywork. But its still busywork and I don't why I'd ever want to do it more than a couple times (once I know the general process)

I wouldn't consider it busywork. You don't have to sit and wait for the progress bar to move. Start the installation and go for lunch.

That's if the installer is designed well and all the questions are front-loaded. Unfortunately not all installers are... Heck, I think it took Microsoft until Windows Vista to do it for the OS.