Advice number one is, of course: Don't. But in case you (or I) still do, here's a few of my notes on dealing with Microsoft Windows. Probably programming related. As usual, this will probably very slowly build up over time and might get split up if interesting stuff comes up.

Another curious thing is ReactOS, which is a sort of reimplementation of the APIs on a more or less free ground. Why? I really have no idea, but it might be an interesting emulator in case it ever gets far enough to run anything really tricky.

Otherwise, Wine is a handy shim that makes running many Windows apps possible on matching processors but different kernel underneath. Once upon a time (ca 2010), I actually used mingw on Debian to build a little application using FTDI library to talk over SPI to a radio chip. I tested it using Wine, and deployed on Windows XP. I expanded on that to use a similar application with a different radio (TI Chronos) but using Windows serial port API. I don't remember if I ever ran that in Wine or just used MinGW on Windows to write and test on target hardware.

Useful tools

Piriform CCleaner is handy for mopping up cruft (and privacy leaks) in temp files and caches and registry.

Zadig lets you assign common API "drivers" such as libusb to USB devices and avoid the usual Windows driver hell.

PuTTY gives you ssh, but also a fairly decent serial terminal. The connection dialog and settings are pretty clunky, especially on a laptop. It is possible to make shortcuts to start sessions that you need frequently. WinSCP is a nice complement for file transfers.

MobaXterm tries to be a more complete thing including even an X server. I haven't really had much use for it, though.

MPC-HC is a clean and featureful native media (video) player. It, or something like it, used to be handily bundles in CCCP along with missing codecs for older windos versions. There's also VLC, which may be useful because it carries its own codecs and doesn't depend on the system ones or share their bugs. It also has some streaming and transcoding features that might come in handy. GStreamer also runs on Windows and can do wonders even with a bat file and gst-launch (no proper coding needed). There's also avidemux.

MIDI support in Windows is terrible, but software is plentiful. Especially there are tons of softsynths and effects. The non-commercial ones are often better than commercial ones and don't come with evil installers and DRM, which in itself would make them better products. SQ8L is a particularly neat thing. Check vsthost, ASIO4all. One synth challenge and Going all Freeware should be mentioned here. See also: LMMS, musescore.

Python can do wonders, even if Windows makes second a class citizen of any non windows-specific code, language, or environment. I posted an answer on SO for a Windows python3 GTK3 development kit that contains useful links for Gtk3, which works nicely. Matplotlib and pyserial are also engineering favourites that make a lot of interesting cross-platform applications quite easy to write.

For electronics, Kicad is also available for Windows. LTSpice can be handy for simulation. Sigrok drives analyzers as usual. Many of the flashers are the same.

Classic UFraw and Gimp are available. Photosift can be handy.

Modeling is easier to come by than CAD, as usual. Still, there's at least LibreCAD, Wings3d, Blender, OpenSCAD, and Cura. Inkscape and Libreoffice for flatland stuff.

Firefox (and Nightly) with uBO and uMatrix

Other needful things: 7zip, mingw, IDA. Vim.