Upgrade from SQL Server 2005 to 2008

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SQL Server 2005
SQL Server 2008
We're in the process of upgrading our servers from SQL Server 2005 to 2008. It's also running on Windows Server 2003 but we're planning a migration on that too. This will include: Log shipping, packages and reporting server. But here's my question: Should we be worried about the risks of this upgrade? What can we do to make sure this goes through smoothly?

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