15 years ago I considered switching to Linux. I depend on some Windows applications and, above all, I want to play games. Wine looked like it was almost there, so I intended to give it another try next year.
Year by year I've been trying Wine again and again. As of today, it's still almost there. So, maybe in 2030? By now, I'll stay using Windows.
For years, I've been reluctant to use Wine wrappers like PlayOnLinux, for no reason other than I don't like wrappers. I always ended up getting everything working with bare Wine, but at the cost of long hours (sometimes even days) of experiments.
I've started using Lutris a few months ago (I gave up on getting Wine and DXVK play well together) and, well, that's a life changing experience so far: everything works out of the box. I has taken all the fun out of Wine configuration for me ;)
If all your games are available in Steam, I see no advantage in using Lutris: in my experience, Proton works very well out of the box.
For games that aren't available in Steam, Proton is of little help AFAIK, and that's where Lutris shines.
Also, some people like having all their games in a single place, in which case Lutris may be a solution too, even for Steam games. As my “single place for games” is my shell, I usually skip Lutris and Steam GUIs to start games directly anyway, so…
12 years ago I considered using Windows. I liked some Windows applications and, above all, I wanted to play games. Windows looked like it was almost there, so I intended to give it another try next year. Then Vista happened.
As of present day I am a happy Linux and Wine user and don't plan on switching to anything else.
You keep changing the goalpost. Odds are if you were willing to live with the versions you were using 15 years ago you would find Wine works just fine. Probably even if you just stuck with the versions you were using 5 years ago.
If someone wants to use Windows applications to interact with other users, using a 15-year-old version is really not going to cut it. Office, Photoshop... all of those big ticket Windows apps have added a lot of things in 15 years. You could get that level of compatibility from Libre Office and GIMP.
Some even earlier directx games are damn near unplayable anywhere but real hardware, last time I checked. Heavily tied to a handful of video cards from a span of just a few years. Looking at you, Mechwarrior 2: Mercenaries. I don't think VirtualBox even works in those cases.
Year by year I've been trying Wine again and again. As of today, it's still almost there. So, maybe in 2030? By now, I'll stay using Windows.