True but webpack itself had a ton of churn and made practically no effort to maintain backwards compatibility causing a ton of work with each major update.

Hmm, I am using it since v2 and I disagree, it was not so bad. I saw a lot of people had overcomplicated configs that could be simplified a lot, I guess those had some problems upgrading... But mine never had much problems (and not just because my needs were simple...), I just removed some options when going to v4 and that's about it.