I'll go first, mine is JIRA. It gets in the way, and things generally go there to die out, tons of information lost forever. I've seen whole product backlogs deleted to never return.
Apple OS X GUI.<p>Everything is dumbed down and mixed with weird usage patterns just because they are different (actually because of patents).<p>Mouse right click?<p>Sorry, MS got the patent, so we will sell you Ctrl+click or two-finger click as a “better” alternative. Can’t make a two-button mouse as well, so you will need to lift your left finger for us to recognize that this click is actually meant to be a right click.<p>Window expand/collapse?<p>Sorry, someone probably holds a patent on that, so we will just make that button to switch app full screen, instead of maximizing a window. Don’t ask what the plus button does on a window - it just resizes it randomly.<p>Hit the Enter key to get into a folder in Finder?<p>Sorry, someone probably holds a patent on it, so please double-click or Mac+O.<p>Want to connect your iPhone X to MacBook 2007?<p>Sorry, you will need to update the OS to get latest iTunes.
Oops, your hardware is unsupported, so you can’t update to the latest iTunes.
Ironically, Windows 7 on the same machine in bootcamp can get the latest iTunes.