Sequence of events for me: 1) stopped using the GOAT compiler GCC 2) killed X11 support 3) killed all 32bit support. 4) hit rock bottom.
2) XQuartz took a while, but is doing well.
3) was a big one in making upstream wine not work. with wine32on64 you can sure still pull the pinball party trick, but building that thing takes too much.
4) was specifically SIP for me, especially when they started making updates break with system changes. The ntfs-3g automount thing has always relied on replacing mount_ntfs [which is, by the way, not the proper way to make an fs on a Mac -- there's some filesystem bundle business], and now it's too much of a pain to still access the Windows drive.