Crossover may be less buggy for applications that are under support, which means that if your application is under support you can expect from one version to the other that you will be able to use it at least as good as if not better. However, crossover's improvements do get back if Wine if they are not too much a hack. However for an application to be supported, it must have enough requests for it (votes) or work well to start with. If your application is not supported and is not working well, you are better off hoping with wine that, due to the more frequent releases your problem will be fixed earlier. This means in the end: if your application does not have enough votes for it, you will have to do some debugging yourself under Wine if you want your application to have a chance to go into crossover's support where it will be looked after that's it does not get broken again. imho comparing Wine and Crossover is comparing apples and pears, they are both fruits but have differents targets.