i think one thing we can agree on is that the only thing users hate more than change is breakage.
rewrites are a valid tool in a long-term strategy, just as debt is for finance. but for most people, incremental change has a bigger, smoother RoI. it sounds like this is kind of what KA is doing. although the timeline seems aggressive and the whole thing absolutist, being stuck on Python 2 is a risk now, too.