Just anecdata, but the few things I use via Wine have all worked fine. I use yabridge so I can use windows VSTs in my Linux DAW.
Games (if they don't use kernel level anti cheat systems) are all flawless with Proton.
But, I honestly don't have a need to use much other windows only software. Almost everything I need to use has Linux versions, or alternatives that fit my needs.
I still have problems running some VSTs with yabridge (could be fixed in an afternoon, but it's important that people should know that it's not a plug and play experience).
What do you use in Windows? It's probably easier starting there and then working out what you can do about it.
Games work great in Proton. Valve has gone all-in on Linux and I suspect before terribly long we'll see more stuff that's SteamOS native, with a compatibility layer for the people who are still using Windows.
I would suspect now that most people either play games which will mostly work okay from Steam, or use stuff that just works in a browser (and I'm kind of lumping Electron apps in with that). Then there are things that are never going to work all that well in Wine or have a native Linux port but which might be worth looking into something else for, like switching from Premiere to Resolve for video editing.
Bar a few exceptions (gaminh mostly) you'd have a much better experience switching to native linux apps. Most are really good once you get past the resistance to change. It takes a bit of time to get used to some but once you are set you are no less productive.
I did the switch 2 decades ago and except for my annual 3 weeks of gaming, I never use wine nor do I use or feel the need for a win VM.
What windows apps do you need? I switched full time to Ubuntu about a month ago and haven't missed a thing. I thought it would be harder, but after some usability configuration changes like how the mouse scrolls, some browser keyboard settings, system font sizes, and logging into a few accounts it has been snag free. Oh and I did install Microsoft fonts. I hate most Linux fonts. The biggest change really is just getting used to new icons. There are several features in Ubuntu I vastly prefer over windows, like window tabs in the file explorer for instance.
So does KDE's Dolphin and many others on Linux. Linux had tabs on file explorers well before Explorer did as well as virtual desktops, app stores, and a few other things that Windows didn't have but later implemented.
Bit of a mixed bag for me. There are a lot of things that work remarkably well, but I have some issues with GPU performance (Cyberpunk 2077 just doesn't run well on Linux for me, despite running great on Windows on the same PC, and GPU-heavy apps like Insta360 Studio and Topaz Denoise run excruciatingly slow or not at all) and some things just don't work (my audio VST plugins work alright, albeit with some bugs about window position handling, but I can't get some of the licensing apps to work under WINE).
Anything that needs a driver isn't going to work. At my last job I needed to talk to some motor controllers and BMS systems through impressively terrible Windows software using proprietary device drivers. I had to keep a Windows partition around on my machine for this. I did have limited success with QEMU, but I never got it working quite right.
SteamVR works ok, but last I checked it still performs worse than on Windows. If you are feeling adventurous, you can try a FOSS VR stack [1]. It works for Steam games running Proton and when it works it provides better performance. I had some troubles with it, sometimes you need to switch versions or you get some artifacts in games, or some games just don't work at all. Good thing is, switching between FOSS and SteamVR is as simple as launching either first before starting the VR game in Steam.
I guess the Linux VR stack might get a bit of love from Valve for the Steam Frame, so things might improve in the near future.
SteamVR for Linux requires DRM leasing to function and many Linux distros, well... window managers/compositors do not support this. But yes it can work.
I hardly want to run windows apps at all, but I have a garmin etrex 32x and I can't for the life of me get garmin windows software to run on wine or linux crossover (something to do with USB) and there is nothing available on linux that can talk to the device. I'd run Windows 10 in a VM but I looked (I think?) pretty carefully and valid Windows licenses seem to be well over $100, cheaper to use a refurbed office desktop.
Someone stomp me down and tell me I'm wrong, please.
Office is easy to get rid of on a personal level through alternatives.
On a professional level the online office 365 web apps are enough for 99% users. My comoany do not even bother giving us licenses for the desktop apps so linux and windows users are on equal term really.
It’s been 4 years since I even took a good look at it.