Honestly, broken saves has only ever bothered me if the game is a grindfest. If the game is actually enjoyable I would rather just start a new game with each new version anyway. Most of the time there's not really any reason that a new update would break saves anyway. I think the most common reason would be if you go back and change something from a previous version so that people's current saves have their character in a status that is now impossible in the new version.And then suddenly: saves break, or even projects get aborted because suddenly too much work to be done.
For instance let's say the dev decided the previous version made it too easy to fuck your mom or your sister. The new version makes it harder by inserting additional requirements/events to get to that point. But now you have a save where you've already fucked them without having completed some of the requirements needed to do it in the new version. So certain checks in the game will either return errors or your status will just generally be messed up. Another common one would be something like adding an additional variable for something that gets tracked as the game progresses. Except now you have a game where you already progressed without tracking that. Depending on your code, that variable might not ever even get defined unless you start a new game.
I would rather have the dev decide ok this new version requires a new save because keeping saves compatible would require adding a bunch of complexity to the code that does absolutely nothing for someone starting a new game. You don't want to double the amount of code just to preserve save game compatibility.
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