If everyone thinks you're off in the wilderness, you might want to check yourself, maybe just a bit.
2. These packaging systems were all designed by and for developers. Debian was designed by and for system administrators. The fact that there are common problems is not surpising.
Of course, it's the debian maintainers' prerogative to structure things such that others generally pick up their toys and go play in their own sandboxes. I just get irritated when I hear people griping about it when it happens, as if system-level package managers have some kind of inherent priority.
I'd say that it's more that if there's no (current) way to track what the other package management system is doing on the distro (any distro, not just Debian) then they can't tell what packages are installed and hence whether the distro-supplied packages can work with them...
It does seem silly from a rubyist's perspective but their approach does make a heck of a lot of complicated software work together in a way that makes administering complex server setups a doddle compared to how it could be.
There's just a yawning philosophical gap between how the Debian and Ruby communities look at the world and approach software management.