WTH is it so hard to "catch up" if you've skipped a lot of HA updates? (re: breaking changes)

Looks like there’s a lot of requests for different versioning strategies/ requests for a LTS branch.
And while I get the desire for those, they create a lot of ongoing work for the team.
A smaller ask that might help users is adding UI to do incremental updates.
If my HA is several months behind, it’d be good if (from the UI), I could update one month at a time, to reduce the workload of addressing any breaking changes (ie: spreading it out, but still making catchup progress.)
Even better, if the update it could highlight/offer the latest version without any breaking changes that might affect *my current install." (Just at the integration level, not by determining if a particular breaking change is actually impacting.)
That way, as a user, I can get to that version, address the relevant breaking changes without having to sift through a bunch of release notes, and continue my upgrade journey as my time allows.