I've had really good luck with Brother and Ricoh printers. From regular computers, network printing works very well (from Windows, Mac, and Linux), and their Android apps are also quite good (though they don't support the native Android printing subsystem, so I have to "share" files to them).
Anyway, my wife is OK with physically connecting to the printer and I almost never need a hard copy.
I was recently trying to print from Windows inside virtualbox on my Mac to a wireless Canon printer. After installing bonjour, Windows found and install the drivers for the Canon but when I "printed" to it only a blank page would come out. Sigh, so close.
That would explain why the machine with iTunes works. Windows isn't my daily driver anymore but I'll definitely try that! Yeah Canon printers always seem to work after installing the monolithic Canon drivers, but tbh it just feels wrong.
Printers using that INSANELY over complicated Web Services for Devices (WSD) seem to have a huge footprint on Windows PCs, are resource intensive, require extra running services on the PC, seem to have a hard time with multiple instances of the printer on the same network, etc.
Maybe a printer that can fold and launch paper airplanes....
I think Apple, MS or someone else must come up with a good printer and kill rest of the printer industry.
Ink is expensive because again: Most people don't print much, and most people have printers that that have some very specific ink cartridge and will blindly buy the manufacturer brand ink because it's easier that way.
If you print much, pay for a reasonable laser printer, and your experience and cost per page are both much better.
They did: https://en.wikipedia.org/wiki/LaserWriter
Everything since then has been garbage.
I try get my family members to use USB printer over wireless when possible as well. Wireless printing is more prone to failure, as chan happen when a wireless device changes IP, SSID or password.