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muddysneakers: I can't save in The Cat Lady. Not technically game breaking because I could theoretically beat it in a single playthrough but really discouraging.
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tinyE: I think that counts as game breaking.

Technically you can beat ANYTHING in one playthrough. :P
There are saves online at the start of each chapter so this one might be doable.
Good Ole Rainbowvision for older DirectDraw games.
Far Cry's last update made it so that enemies could see through tents and shoot you with perfect accuracy. It was never patched. The tents used to provide concealment and made it possible to sneak around. But now you have to play the game in a more run and gun style.
I happened to discover another one when playing around with Bard's Tale 2 (in particular, transferring characters from the Apple 2GS version to the Commodore 64 version):

In the Commodore 64 version, special party members will not use spells or breath weapons when enemies are around. This, among other things, makes the Wind Dragon and Wind Mage spells useless for the player. It also makes one of my favorite aspects of the game, collecting monsters with interesting and useful abilities, significantly less fun.