If you are migrating your SQL Server 2000 code base to SQL Server 2005 or 2008, the effort you need to take in 2008 will not be much larger. Although there are some features in 2008 during 2005, the difference is not as great as the transition from 2000 to 2005. I would suggest going straight to SQL Server 2008 with the following main pros and cons of the solution:
Pros of the transition to 2008
You get another 3 years of life for your systems almost for free. SQL Server 2008 will support longer than SQL Server 2005. This gives you more time before you have to upgrade. IMO is probably the strongest argument for migrating to SQL Server 2008.
You get some features, such as geospatial indexing, that are not available in SQL Server 2005. Although your SQL Server 2000 applications will not use these features initially, you will get more options in the future without performing another platform shift. It doesn't matter to your carryover exercise, but you buy yourself a little flexibility almost for free.
Pros of migrating to SQL Server 2005
This is less of an “edge of bleeding” than SQL Server 2008, so the implementation path is likely to be a little easier.
Attracting people who can work with SQL Server 2005 will be easier than experienced SQL Server 2008 users. However, it is likely that you will mainly retrain your employees, so this is unlikely to be a serious problem.
YMMV is in some of these points, so you can do a more detailed study of potential problems and see if there are any real benefits or obstacles specific to your circumstances.
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