Dean, I seldom comment in this "PTC Community" but I fully support what you have said. I am only 2 years behind you in PTC experience (rev 6, I think and 24 years) and I mostly manage now rather than drive. I have found the thing that can be most destructive to users - new or experienced - being bombarded with negative comments about the software being used. Nothing will discourage users from finding answers or learning something new more than the constant threat of bringing on a new CAD package. On the other hand, nothing boosts the enthusiasm like finding a solution to a problem. So at the very least (anticipating the comments), we have the opportunity to create a lot of enthusiasm...
The last company I worked for had all the things you talked about and we did some amazing things with ProE. Sure, there were a lot of stumbling points but we worked around them for the most part. We even got some issues resolved by opening calls with PTC.
Anyway, thanks for your response. This is an interesting thread.