Funny... OpenBSD suffers from dependency hell just as much, and still relies on it to manage its own ports/packages ?The fact that pkg says that it is going to remove a package and asks yes/no is hardly relevant.
If you say "no", then you will prevent security updates for all other packages. An operating system advertising with security can't rely on that.
But yeah, this thread is a great use case for Poudriere - we should be able to just download the Libreoffice port (via git) and compile it against the existing stuff so that upgrading is not so damn scary. I'm trying to pull off that idea with KDE, although that project got shelved for me (real life got in the way).