First, anything Adobe. I haven't run Wine in a really long time. Maybe it has progressed with Adobe software runs acceptably now? Don't know, but there have been other non-dev centric and mainly video centric type apps that never worked on Linux. After that, Windows v Apple. For me and what I need to do, Windows loses every. single. time.
Now, I'm an old dog not interested in learning new tricks unless it will absolutely postively without a doubt be money making for me. Doing for the sake of doing is no longer something I'm passionate about. I have other things to spend my time that is much more deserving of my passion. That's what the young kids are for, and then brag about their accomplisments on a Show HN. Then I can decide if it is worthy for me.