There is plenty of material available to help you upgrade to SQL Server 2008. This blog is intended as a short list for the most useful guidance that I have found. And you may have different experiences upgrading from SQL Server 2000 and SQL Server 2005
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Some customers prefer to upgrade to SQL Server 2008 by detaching all databases from their SQL Server 2005 instance and then reattaching them to a completely new SQL Server 2008 instance. If you choose this upgrade strategy, you should be aware that you
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