I have never (yet!) gotten myself into any trouble, by following a very simple principle: if aptitude (dselect back in the day) wants to remove or hold more than a handful of packages, STOP. Undo what you just did, and instead of a bulk upgrade go through marking one package at a time for upgrade. When you hit one that needs major changes, if you can't find an upgrade alternative that is sensible, leave it un-upgraded and try again in a few days.
This time upgrade has been one of the more challenging ones to track in unstable, but patience and actually reading the reasons that dpkg reports for why it wants to do something has gotten me through it.