I was just installing updates to my VMWare Workstation 10 and the process was a big pain in the patute (to put it mildly.) Just to illustrate, the installer had me first uninstall the existing version of VMWare and then began the installation from scratch, like if I was just installing it for the first time. It's OK if it does all this in the background, but showing windows like this:
does not make it simple. For instance, it's been a year since I installed it so I have no idea what configuration I originally installed it with, nor that I know off the top of my head what all this mumbo-jumbo means.
So please automate your update process and make it less painful. (If you want to learn a good example, ask Google engineers and the Chrome team. They know how to do painless and user friendly updates.)