With 32-bit program support going away on the Mac with Catalina we need to start seriously figuring out how to have WINE run on these newer systems so that reasonable instructions can be provided.
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Right now we can use VMs (VirtualBox, Parallels, VM Fusion) using other operating systems (Ubuntu, Red Hat, or if you can actually get it to work an older version of the MacOS) thought doing this correctly is kind of 'uhhh, how do you do that?'Wineskin Download For Mac
Currently Wine still requires 32-bit code to run 32-bit Windows software, which is a problem for Catalina (which dropped 32-bit code support almost completely), and cannot be solved with a simple recompilation. It's only possible to use Wine for some 64-bit Windows software. I can't find any recent posts about this. Is it possible to compile Wine in 64-bit mode for Mac (or even Linux for that matter)? The Wine used in PlayOnMac and WineBottler is 32-bit, which suggests that it can't be done.
But is that the best (ie easiest) solution we can come up with or is there some other method on the table we could use?