Most printers with networking capability work well these days. Some even entirely without drivers (thanks to Apple for once). HP should be fine if it’s relatively new. Older printers can be a major pain in the ass.

Scanners access is now also finally easy with AirScan (again thanks Apple, and I don’t say this often), so some devices might just magically work. More likely you’ll need to edit a line or two in a SANE config file somewhere or deal with the horrible web interface of CUPS to configure the printer, but with the right device, there’s finally no hunting for drivers on obscure web archives of Chinese manufacturer pages anymore.

It seems when you have a terrible attitude of entitlement and no willingness to learn, you’ll never be happy with anything. Huh.

In that case, I’d rather have him stay unhappy on Windows and not make those videos anymore.

There is a crossover between the two, for example the Mass Effect Mod Manager and things like that, which work adequately.

Wine works well for most small GUI applications, the biggest issues are with the huge corporate, commercial programs like MS Office, CAD software and Adobe crapware, for which there are ways to get them to work, but you’d be better of migrating to a native alternative.

C# apps are always a pain though. Mono is rarely enough and as soon as you need MS dotnet libraries, everything is going to be a lot more painful.

OT: At my previous job I ran a Windows-exclusive compiler toolchain (Keil C51) with wine in a Makefile, which was a huge improvement to developer workflow compared to everyone having to use the bundled IDE, especially due to the parallel builds. Wine is awesome.

Emacs is actually a real GUI application. It has font sizes, variable width fonts, image display, etc. and with the pGTK backend even native wayland support. It also has a rendering backend for the terminal, and some people have their reasons for using it, but the default and general advice is to use Emacs in GUI mode.