IT Dimensions
"Over 66% of enterprises are not confident their organization has a single view of their legacy data, while they recognize that data quality is imperative to business and compliance "
NCC

SQL Server 2005 vs SQL Server 2008

PROS - SQL Server 2005 PROS - SQL Server 2008
Mature product with most of the potential issues addressed Longer support and longer time before moving to newer version.
Implementation path will be easier New features such as geospatial indexing that are not available in 2005
Window for stabilization, tuning and removing legacy code  
More skilled people with SQL Server 2005  
CONS - SQL Server 2005 CONS - SQL Server 2008
58-80% repeated effort (process is reused but testing effort doesn't change) Major changes for both DBA and developers
Two downtime windows More intensive testing required because of deprecated features
Lacks latest capabilities More downtime because of the above
  Many bugs are not discovered. Longer wait time for the corresponding packs or hotfixes.

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Data Quality