When both will run the application you need, the main difference is several hundred dollars. That is to say: you still have to buy a full license for Windows to use it with Vmware, whereas Wine is a free re-implementation. To people who left Windows because of MS's unfair business practices, their habit of putting the wants of IP publishing conglomerates ahead of user functionality or fair use, and general feeling that their customers are always assumed to be a pirate... this is of course unacceptable. Vmware _will_ be more compatible, because it's running the original Windows code, but Wine integrates better with the native OS. Now you can run the popular vm's in an integrated desktop mode, but you still have to launch that virtual machine and segregate your program installations accordingly.