Depends really on the games and software you require.

For games, check:

• https://www.protondb.com/ - people post their experiences with games if they work or not.
• https://areweanticheatyet.com/ - lists of anticheat enabled games which work or not.
• https://appdb.winehq.org/ - wine's appdb has games and general applications listed, with some info on how they work or not. Some info is absolutely ancient at this point.

In general, indies and singleplayer games generally work fine. Battlefield/Fortnite/etc hugely popular multiplayer stuff with kernel-level anticheats generally doesn't.

I've only ever set up few printers to work on linux, and they've been bigger office printers. And they've all worked with minimal effort. Absolutely no idea about home printers.

edit: as for windows software support, generally win-apps run on wine. Some really well, some with issues, and then some just dont. Afaik eg. ancient versions of Photoshop run, more recent ones don't.

I run a windows version of a music software (renoise) because my effects/instruments have only windows versions. It works, but performance isn't quite as good as it was on actual windows.