I've experienced multiple instances where (so I heard; I don't use Windows) a Windows Update completely broke a game on Windows for everyone, but Wine/Proton kept running it just fine. So we're already there in some sense.
What I wonder about is if MS wants to keep people on windows, what methods they can use to do that. For simple desktop stuff I don't think they have many options to lock in other developers (and their audiences) to windows unless they want do so themselves (putting aside web based or not PC-desktop).
Bleeding edge gaming and multiplayer anti-cheat is one area where I think having a big company owning the OS probably helps them stay ahead, as that structure probably lets them work with hardware designers to get the capabilities in use (i.e. in new versions of DirectX) and available to software developers first. There's generally a lag in adoption for new features within Vulkan and then usage downstream in wine/proton to get compatibility parity with windows, then the games themselves being able to run feature/performance parity. It'd be interesting to see what cooperation would be needed to have the linux gaming stack equal at the point new features are released, and with the least amount of manual hacks or command line tweaking required for the users. As discussed a few weeks back, tough anti-cheat for linux seems like a paradox with the current methods.
> What I wonder about is if MS wants to keep people on windows, what methods they can use to do that
Microsoft doesn't give a fuck about private customers any more. They don't have money.
What has money though is enterprise/government sales, and MS got these customers tightly locked in. Compliance audits and tooling for insurances or legal stuff (SOX, GDPR, ...) are built against a full Microsoft stack of MS Server, Active Directory, Azure, Teams, Office 365 and Windows desktops.
You might be able to get away with replacing AD and GPO with Samba servers but even that is already a pain when the auditors come knocking. Everything else? There is no single FOSS based "standard offering" (i.e. a combination of everything needed to run an on-prem enterprise site, Office replacement, remote collaboration tooling), so every audit for such setups must be custom made and involves a lot of extra work.
A second leg is industrial control machines, medical devices and the likes. That's all stuff built by third party vendors and integrators. They need to continue on Windows because switching to an alternative OS would require redoing everything from scratch on the software and certification side. These customers buy the LTSC IoT stuff.
And that is why you see Microsoft pushing enshittification so hard on private customers... extract the last few cents you can from them. But the real money comes from the large customers.
For a while it seemed like Microsoft wasn't taking Windows seriously as a product. And the easiest way to cut costs on that is to use a solution someone else is building and maintaining. They did retire Internet Explorer in favor of a Chromium browser, so it wouldn't be unprecedented.
Anything Direct Draw related will be mapped into OpenGL under Unix giving you decent speeds. On Windows it will be a crawling slideshow because from Windows 8 and up it will use a really dog slow software mode with no acceleration at all, worse than plain VESA. Yes, you can reuse WineD3D DLL's on Windows and run these game in a fast way, but not by default, it's a Win32 port of some Wine libraries.
I had to use WineD3D's ddraw.dll among another one to run these touch based arcade machine games with card games, Trivial Pursuit, hangman and the like. If not the game made for w98/2k would really lag even under an i3.
The same with some multimedia CD's from its day. Scummvm it's partially implementing Macromedia Director support but the mentioned game had a custom engine. The Scummvm devs would RE in few weeks (it's a simple 2D game bundle, nothing difficult, with virtually no animations, almost everything it's still images) but no one began yet.
It certainly runs 16-bit Windows games better than Windows 11, which can't run them at all. Not that there are a ton of those, but it's still pretty neat that they work.
The thing that you're missing is that Microsoft used to ship that emulator with Windows. Then they stopped doing that.
AFAICT, Wine can run WIN16 programs. I don't know if it can run DOS programs. There's a WineHQ wiki page that says it can load DOS programs, but various internet fora seem to believe that Wine's DOS support is pretty broken. I've never tried it, and have no DOS programs handy, so I can't verify those claims.
"DOS support" is tricky inasmuch as a lot software from that era - especially larger and more complex packages - interacted with hardware directly. In a sense, they weren't really DOS applications so much as they were bare-metal PC applications which were booted from DOS. It'd be difficult for WINE to support those, and other projects like DOSbox / 86box / etc do a better job of it.
There is also a port of Wine’s VDM back to Windows called otvdm or winevdm that is able to run 16-bit programs on Windows. It is surprisingly capable, I was able to run a 16-bit VB program that used a serial based optical modem without issue.
Time to dust off my cd copy of Stars! (From the disk backup, the cd had terminal illnesses and has died). The only win16 game I've ever seen distributed on CDROM. Wine already ran it ok (iirc there were some issues but nothing gamebraking), but now it can do so without i386 libs.
MS got such a black eye for that that they're developing a build of windows specifically for handhelds, optimized, without the bloat and power hungry extras. Would be nice if it ran on laptops