Please advice on doing this migration, are there any issues I should be aware of. Can I do an in-place migration of the server or side-by-side?

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Run the SQL Server Upgrade Advisor to check for any compatibility issues.

You can do side-by-side or in place.

Attaching 2005 database files to 2008 will upgrade them.

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I've migrated about half a dozen systems and had no issues.

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+1 I did a couple here in our office with no snags. – Hondalex Aug 26 '09 at 13:47
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