* The company grew fast in 2006-8. I think it went from 500 to 5,000 employees. There are issues that are still being worked out such as making sure the right people are in the right roles and inter/intra-divisional communication. Some layoffs have occurred. While necessary, it is a con. A related con is working with a mis-cast team member, which happens when you have that type of growth.
* VMware product development has academic roots and often displays a lack of Enterprise development process. While the core product is good, maintainability and customer patch/upgrade experiences suffer. Support and support engineering pay the price trying to solve problems that should not exist. Part of this is due to inexperience of the developers in initial product development positions. Part is also due lack of detailed architecture planning. Part is due to the idea that we must develop the product fast to compete with MS/Citrix/etc.
These are not challenges unique to VMware, but they are ones that could be better.