The first problem area is SPD 2010.
It has been confirmed in a thread in the new SharePoint 2010 (General) forum
that it is not possible to edit v3 sites using SPD 2010.
This is against all previous practice (with SPD 2007 and FrontPage 2003) where downward compatibility was available but naturally upgrade compatibility wasn't.
The only slightly bright spot is that it was also confirmed that SPD 2010 and SPD 2007 can be run together on the same client machine. So you don't need two machines just to be able to work with v3 and v4 sites.
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That problem area however fades rapidly into insignificance if you are a WSS 3.0 user using Windows Internal Database.
As such you have a free database system which unlike the standard SQL Server 2005 Express it is based on does not have a 4GB database size limit.
Well it looks as if people who are running this and have exceeded this figure (non-limit!) or about to do so will have serious problems if they want to upgrade their system to SharePoint Foundation 2010.
I don't have any other explanation that in yesterdays massive batch of over twenty KB articles on the "Pre-Upgrade Checker for WSS 3.0 SP2" two of them are about the Windows Internal Database and both of them are about warnings that you get if you exceed 4GB in the size of a database "The large size of a database can prevent it from being upgraded".
Doesn't this seem to you as if Microsoft with SP Foundation 2010 intend to go back to the situation with I think WSS 2.0 and have a size restriction on the database sizes of the basic installation of SP Foundation 2010?
It's a clear indication of this when the only databases that throw up this "problem" are those using Windows Internal Database. There are no equivalent KB articles for databases over 4GB using (say) SQL Server 2005.