Situation – Server running windows server 2003 and SQL Server 2005. About 18 various databases on the server. We need to upgrade to Windows Server 2008R2 and SQL Server 2008. We can't afford to lose any of the databases (if I did my life as I know it would be over…)
What's the safest / simplest way – and how do I get all the users and roles done as well?
Best Answer
You can use the "upgrade in place" feature of SQL Server 2005 to SQL Server 2008. IIRC, you can also use the Windows Server 2008R2 installer to upgrade from Windows Server 2003 because Windows Server 2003 is only two versions back.
This answer focuses on SQL Server. I recommend that you do a couple of things: