Serato DJ should work in Wine fine. Wine is more active as a project now than it ever was, thanks to Valve’s Proton, which is bascially a Wine fork aimed at gaming on Linux through Steam. But, they push changes upstream (the Wine project), so Wine is really going fast forward now, they’re up to version 8.something now, which is a big jump, considering it was at version 5 only a few years ago and that the project has been around for about 2 decades.
Regarding DJ controllers and Wine… that might be a bit tricky, but it’s worth a shot 🤷. Might require some manual library overrides or setups, but if the controller is supported in Linux (works fine with, let’s say, Mixxx or Transitions DJ), it should be able to work in Wine as well.
Some file managers might add the +x automatically if you choose to run the binary through the desktop environment (not the terminal)… or ask you if you’d like to mark the file as an executable (i.e. add +x to permissions).
You can’t do it the same way with tar, what are you gonna execute, tar is neither a script or an ELF binary. It’s like asking for a zip file to be executable, doesn’t make sense. You can change the extension to .exe, but it won’t run, it’s not an exe, no MZ header, nothing 🤷.