Short answer 'Yes' - you should be able to do it all in one swell foop.
A new release typically copies over new templates, but the databases are left untouched. Then the design process updates the database design from the templates.
As long as your directory structure is the same, and you copy over all the database files, templates, and anything else you'll need.
Then do an install (reinstall) of Domino over the top.
I've done exactly that multiple times in the past.
At a high-level what I would do is:
1) Install the Win2008 machine
2) Copy the Domino data directory to the new machine
3) Copy the notes.ini to the Notes directory
4) Install the new version of Domino over the top
Short answer 'Yes' 
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. . Short answer 'Yes' (Mark Taylor 2.Aug.12) 
