With Big Sur I finally did my first fresh install of macOS since Jaguar (10.2). It took me an entire weekend and while it’s nice to have a clean out I think I’ll just do a time machine restore when I finally get an M1 Mac.
I'm not talking about apps that you got from the app store or similar, but, rather, things you installed via homebrew!
When I temporarily had to move back from a more recent (~2014) mac to an older one (~2012), I got bitten by that becuse some apps installed via homebrew had been built from source with optimizations that the older machine didn't support. It was easy to fix, since I could just reinstall them as I saw them breaking, but it was an annoyance nonetheless.