While I agree that there is always more information and best practices 6-12 months out, but the feedback from the partner network has provided a lot of real world feedback. In addition, there is more documentation and guidance leading up to the launch than I've seen with any other major software platform. The decision to upgrade or implement will depend heavily on the businesses objectives, budget and current project capabilities. I have seen a number of customers comparing large customization efforts in 2007 with out of the box features in 2010. When you add in the complexity of having to port those customizations later the cost and risk of going to 2010 now is much more attractive.
I think this is a great topic. I personally do not hold ISVs to the same standard since their experience and interests may or may not have anything to do with the publishing features, but the partners should showcase their experience through demonstrations with their public facing site.
A few years back I worked with an org that used MS's Project Server which seemed to do a good job of managing the individual projects as well as the overall portfolio. These days I'm trying to deploy project sites in SharePoint (MOSS) which gives a collaboration and tracking space within the a project team and then provide mechanisms to aggregate that data across the project portfolios for a given group, division, or across all units.
There can be a lot of value gained from the information, but it can take a lot of time to get everything setup. There seems to be a lot of overhead at first, but once in place it reduces duplication and makes reporting so much easier.
One of the biggest project impacts I've seen is with resources shared across multiple projects. When projects are managed and tracked individually it can be hard to see future risks. What if the same resource is working a critical issue on two projects? What if the combined allocation for a resource is 300%? You can only see these issues when looking at everything at once.
Your quotes and comments about management not knowing what IT does is scary. As outsourcing becomes more prevaliant roles will change. Even if you outsource development, you should still have a tech lead in house to validate what they are doing and make sure it fits into your environment. This also means internal QA, PMs and perhaps Analysts are needed.