> So how hard is it to just automatically add the uninstall to the upgrade process? Make it optional: after completing an upgrade, ask the user whether they'd like to remove IE or keep it.
I would say "pretty hard". Not harder than some other things they have to manage, but you are looking here at functionality that affects a complex operating system. Having the system without IE for a clean install is relatively easy: you have a stable configuration made, then install it and test it.
Having an old system (with who knows what running on it) upgraded, is pretty damn complicated (you have to change more than a Gb of files without breaking dependencies); when you add removing something from it that was critical to the OS in the previous version (if we are to believe MS that is), that should increase the risk of breaking stuff quite a lot.
From the "project management point of view", you're looking here at adding at least some man-days of testing for this feature to weed out bugs from this alone (out of the top of my hat I would say some month or two in man-days, with all that's involved in the upgrade process). A competent manager on a budget will probably try to avoid adding that feature if there is no distinct need for it.
I'm not saying it shouldn't be done, but saying "how hard can it be" might be an over-simplification.