According to some conversations I've had with folks, Drupal 8 seems to be even worse than Drupal 7, and Drupal 7 is literally the worst upgrade experience I've ever had. Piles of new jargon and new APIs get introduced in every new release, and often replaces or subsumes entire swaths of similar functionality in previous releases (e.g. nodes -> entities), and Drupal was already ridiculously jargon-heavy to the point of documentation making no sense to someone without extensive experience with the specific ways they use terminology, and googling generic terms like "node" and "entity" is a laughably unhelpful process.
I have, at many points in this process, thought: "Fuck everything about this, I'm migrating to WordPress." I probably should have done so the first time I thought that, as it would be done by now. But, every time I made it over another hump in the upgrade, I thought, "Surely that was the worst of it." and kept slogging along. Upgrading WordPress is literally a no-brainer, now...you just get emails every week or two saying, "Your website has been updated to the latest version of WordPress." Sometimes, you click the "upgrade database" button.
Sorry to rant. But, I happen to be working on my Drupal upgrade again today, so I'm grumpy.