Windows Server 2008 took some steps towards helping customers with best practices by increasing the default security of roles installed via Server Manager.

Is the server running Windows Server 2008 R2? Is it exclusively used as a SQL server? If both answers are yes, you should leave it alone.

In-place upgrades to SQL Server 2014 are supported from SQL Server 2012 SP1, 2008 R2 SP2, 2008 SP3, and SQL Server 2005, but are not necessarily the best option.

For those legacy SQL Server 2008/R2 applications that remain critical, some form of high availability or disaster recovery protection will be required to preserve business continuity.