It is kind of ironic that the two Windows applications I missed the most in both Linux and Mac are good text editor and terminal emulator: Notepad++ and MobaXTerm
Perhaps it's just nostalgia, but I feel like 2006-12 (before the Mac App Store took off) was the golden age of Mac software. There were those ~$100 'app packs' that bundled a bunch of different software together. You'd buy it for 2 or 3 of them and end up discovering some cool new software in the process.
Back then, the iPhone was still the companion to the Mac, not the other way round.