A couple of weeks ago, I did a cool test where I took a WSP built for MOSS 2007 containing a not that small site definition, and installed it to a MOSS 2010 environment.
The stsadm tool is still there to help us out so I used it to add the solution. All went fine until I went to the central administration. In the technical preview, the Solution Management page wasn't directly accessible. Luckily for me, I could use the same URL as in MOSS 2007. This presented me with the overview of all added solutions. I then deployed it to the central administration web application so I could use the site definition to create a new site collection.
To my surprise, SharePoint knew that now it had to deploy all files in the LAYOUTS folder to the 14 hive and not to the 12 hive !!
Another surprise: the site template showed up when I wanted to create a new site collection.
Yet another surprise: after waiting for some time, the site collection actually was created based on this site definition. This site definition contains custom master pages, custom site columns and site content types, web part pages with web parts already placed, ... and it all got created without any problems!
OK don't get your hopes up too high because when I actually wanted to visit the new site collection an error occured because there was a problem with the SearchBoxEx control.
I changed the master page so I could at least access the site. I immediatelly checked the content types and site columns because they are created with a feature. They all worked fine!
The fact that it all was created to me means that the CAML language was not changed too much so we can reuse most of our old definitions.
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