I'm not going to argue about old productivity software, but some games do indeed "age badly".
Obviously the game stays the same, but game designed has advanced and, if you are used to play modern games, some problems that are mostly fixed on all games from the last decade become annoyingly obvious.
For me, the main one is controls:
* Once you are used to WASD+mouse for FPS, going back to ctrl+arrow-keys (with some awkward keys to strafe and look up/down) is awful. If you are able to patch the controls to WASD+mouse, some games then become much easier than intended (since they were not designed with circle strafing in mind).
* Controlling the camera in old 3D platforming games is also a pain. It's amazing how long it took to move the camera controls from the bumpers to right the analog stick. The limited ability to control the camera is also partially responsible for it to get stuck in corners a lot.
There are also some level design choices that are arguably bad, but were required at the time, such as loading tunnels or abusing backtracking/repeated assets (e.g. fight all bosses again) to make the game longer.