There is also the ffmpeg kerfuffle a few years back when Debian decided to replace the ffmpeg package with an incompatible and inferior fork. You can imagine the amount of confusion that ensued.
That said, I think Debian's occasional messups are far less egregious and damaging than Ubuntu's though.
There was also that time many, many years ago they decided to remove the ability to load binary firmware blobs for things like network cards in the kernel because of an interesting interpretation of the GPL. :-/
There was zero documentation on the change and the error you received attempting to install an extension was basically "operation failed". I discovered the cause only because there was an open bug about it on the Debian bug tracker where the maintainer refused to acknowledge the problem. Eventually, sane minds prevailed and that stupid patch was reverted.
So, unfortunately - you'll end up having to deal with people that refuse to look at things from the user's perspective no matter what distro you use.
And yes - I'm still bitter. :-/