If there’s a list of Windows programs that you want to run on your Mac, then it may be worth investing the time and effort into setting up a Windows VM, as you’re going to have greater success running Windows software on a VM in the long run. To get an idea of the kind of applications that are likely to run on Wine (and associated tools like WineBottler) check out the Wine Application Database. It’s not all that unusual to encounter Windows apps that simply won’t run on Wine, or to discover bugs in the applications that do run. The downside is that you’re far more likely to encounter issues when trying to run Windows software on Wine, compared to running it on a virtual machine. Wine is easier to setup than a dedicated Windows virtual machine (VM), and will take up less space on your hard drive compared to a VM.
