I pretty much always recommend Linux Mint Cinnamon for anyone entering Linux for the first time or anyone who wants something to just work 98% of the time. I use Mint Debian Edition (testing it out. So far, so good, and it’s quickly entering first place in terms of recommendations, as it seems just as stable and uses Debian packages instead of Ubuntu’s), OpenSuse with KDE (less for beginner’s and more for those who want “eye candy” and some nostalgia), and Fedora Silverblue (currently have an update issue with its certificates, so can’t really recommend it yet). I’ve found very few Windows programs to not work within WINE (more complex, system file dependent programs generally are those that fail), so you may find that all of your Windows-only programs work perfectly fine under WINE.
With Mint (and others, I’m sure), you can install multiple DEs and test them out, then remove those you don’t like. Or keep them all and play DE roulette I guess lol