
I never tried pirating native linux programs, but windows stuff worked well for me. Use some sort of wine prefix manager for this, like bottles. I used PlayOnLinux, but its an old buggy mess and there are modern alternatives nowadays. There is also umu-launcher and stuff that uses umu, which is more for games, but also works well for programs.
The most trouble I had was with installers and setup tools that need certain files to be in certain locations. There is a mod manager for Dawn of War 2 thats an exe that needs files from an installed game, and it was very bad on linux, with missing fonts and crashes. I got it to work with some fiddling however. On WineDB and ProtonDB there is guaranteed at least one person who had any given problem and has an arcane solution, or at least a bug report with lots of information, so try there if you are stuck. Good Luck!
Edit: Here is the WineDB link, seems to work well, but it was only tested up to version 17. https://appdb.winehq.org/objectManager.php?sClass=application&iId=2793

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