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I think that better is to upgrade first PDM because with PDM 08 you can't read SW 09 files.
The documentation on it says that you MUST upgrade PDM prior to upgrading SolidWorks for the exact reason that Faur mentioned. PDM 2008 cannot read SolidWorks 2009 files.
We just finished our PDM upgrade and it's running smoothly so far with SolidWorks 2008 while we're waiting on a few other systems to be upgraded before we can upgrade SolidWorks. Some of the additional BOM features aren't functional, but otherwise it's not causing any major issues.
Where did you find the documantation Is the installation guide?
A few of us were discussing this before we did our upgrade in this thread: https://forum.solidworks.com/forum/messageview.cfm?catid=45&threadid=15348
I can't remember where I found the documentation that said to upgrade PDM first, but I'll look around and see if I can find it again.