Portal 2 is one of my favorite games ever, but it's missing a 64-bit upgrade.
It might be enough to ensure that my next purchase is a PC, despite finding Windows loathsome.
In addition to countless classic games being dead in the water, my Mom was completely blindsided by the change, suddenly losing access to several old-but-trusted productivity apps, and she had to scramble to find replacements. I don't recall there even being a generic warning during the upgrade process, let alone "the following apps will no longer function: [...]; do you wish to proceed?"