Have postgres updates actually been requiring users do migrations? Or is this just a fear that something will go wrong?
A dump/reload of the database or use of the pg_upgrade application is required for major upgrades.
Now, seems one can mostly use pg_upgrade, which only rewrites the system tables[2] so is fairly quick. But if on-disk format has changed it seems you're forced to dump and reload.
At work we've mainly been using SQLAnywhere, which would just disable new functionality for databases using old on-disk format. So upgrading major versions has usually been fairly painless and quick.
I don't think this is done automatically when you simply install a new postgres version, but I'm not certain of that.