Moving from SQL Server 2005 to SQL Server 2008 won't be quite as monumental as upgrading from SQL Server 2000 to SQL Server 2005 (which many organizations haven't even done yet).

However, when i attempt to do an in-place upgrade of SQL to 2008 R2, either 32 or 64 bit, it goes through the part where it checks the Setup Support Rules with no issues.

4. If I try #2 & #3 on a SQL 2005 instance, I get the same failure/success as SQL 2008 R2 5. If I try #2 & #3 with SQL 2012 or SQL 2014 both successfully read the header ...