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Upgrading from SQL Server 2008 R2 to SQL Server 2016

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Hi All ,[moving my question from the wrong forum to here!]We have all application databases in SQL Server 2008 R2 .I am looking forward to upgrade the 2008 R2 databases to SQL Server 2016.Could you please share your experience with this upgrade .What are the challenges ?Please also help in selecting the Standard vs Enterprise based on commonly used features.Thanks!!

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