Yeah, I think it's fair to say that the nadir of software is somewhere in the late 2000s. I'm going to pick 2009.

Snow Leopard on the macOS side of things, Windows 7 on the other, both offering marked improvements in stability and sandboxing over their predecessors. Shareware is booming, the first App Stores have only just launched, Facebook is still that place you share exam notes with your college classmates.