> I've been bitten by Debian packages being years out of date
I've been bitten far harder by pypi packages trying to download random opaque binaries, miscompiling their own binaries, vendoring and failing to update large packages, having impossible-to-satisfy dependency requirements (relying on pip only ever making a half-assed attempt at satisfying them) and generally making strange assumptions about the target system.
That is indeed also a problem! Essentially it comes down to wrapping sets of dependency management. Thankfully the "engineering" side of Python is fairly good at this in my experience, but I have seen the "data science" side of Python do some of this.
I've been bitten far harder by pypi packages trying to download random opaque binaries, miscompiling their own binaries, vendoring and failing to update large packages, having impossible-to-satisfy dependency requirements (relying on pip only ever making a half-assed attempt at satisfying them) and generally making strange assumptions about the target system.