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I'm using Windows 10 on an Acer laptop.

It would be nice if I could run both Palm Desktop 4.1.4E and Palm Desktop 6.2.2 at the same time. My plan for now is to run 6.2.2 directly, and 4.1.4E inside Wine inside Xubuntu inside VirtualBox.

(Yes, ReactOS is also an option. But I'd rather use Wine than ReactOS.)

It would be better if I could run Wine on Windows directly.

Does Wine work on Windows? If so, how well does it work?

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    This looks like an XY problem: Your main problem is to run two copies of the same app side by side. Your solution is Wine. It is a bad solution. There are a lot of application virtualization and sandboxing solutions that do it for you. – user477799 Mar 12 '17 at 5:30
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    I've found Sandboxie to work well for this. – PunctualEmoticon Mar 12 '17 at 8:14
  • @FleetCommand: Intriguing. "Application virtualization". I've never tried such a thing, and didn't even consider the idea, but maybe I shall! Thank you. – unforgettableid Mar 15 '17 at 15:24
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The old official Wine wiki ran on MoinMoin. It included a page about running Wine on Windows. (The current official Wine wiki runs on MediaWiki, and appears to include no equivalent page.)

Thanks to the Internet Archive's Wayback Machine, you may still view the old page by visiting the link above.

According to the footer at the bottom of the page, it was last updated a couple of years ago.

The page says:

Many Wine DLLs can be cross-compiled with mingw-w64 already, but Wine itself doesn't work yet. [...] A working Wine on Windows is way into the future.

So, the answer is this: Wine doesn't work on Windows yet, and it's not expected to work on Windows anytime soon. Too bad.

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You can run Wine on Windows using Cygwin.

https://wiki.winehq.org/Cygwin_and_More#Wine_on_Cygwin

You'll need to install Cygwin on your Windows system. You could theoretically install it to a Wine prefix running on a unix machine (or even within another Cygwin install within ... ad infinitum), but let's stick to one heresy at a time.

  • configure may fail to detect many packages even if you've installed them; there doesn't seem to be an open or closed bug-report about this though
  • 16-bit components had severe compilation problems so Wine now builds with --disable-16bit by default. Getting those to compile might be a "fun" problem
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Yes, you can. Inside Windows, you simply set up a virtual machine like VirtualBox from Oracle running Linux. You set up the Virtual machine to use both accelerated 3d and accelerated 2d graphics. All Virtual machines inside Windows are capable of running with fully accelerated graphics, making the graphics run almost as fast as in native Windows. Since Wine is not an emulation, it will run as fast as any other Linux application inside the virtual machine. Nowadays the virtual machines perform much faster than the specifications necessary to run older Windows programs.

As mentioned in the added comments to your question, you can also use Sandboxie to run instances of applications sandboxed so they don't interfere with an instance already running in Windows. I use this myself to run Skype simultaneously with two different user accounts. The free version of Sandboxie only allows you to run one sandbox at any time. If you want to run more than two instances of Skype with different user accounts, you will need to upgrade Sandboxie to a paid version. The paid versions will allow you to run multiple sandboxes, simultaneously.

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