Am not the pirate that I used to be, but I've found that they pretty much work. Cracks seem fine, repacks make a couple of assumptions that tend not to be true on Wine:

• how folders are arranged

• leaving out all the additional installers for things like .net, because obviously everyone already has them

I'd usually make a new folder for 'what you're installing', create a new launcher for it in Lutris selecting that folder as the base directory, and then use the 'run different executable' option in Lutris to start the installer. Once that completes, you should be able to adjust the config to what you've installed, see if it works. Be prepared to try lots of additional installations with WineTricks, particularly .net and directx.

(To be fair, a lot of legit older games need the same in order to work, if you're installing from CD / DVD and things.)