I'm setting up 1 IIS web server and 1 SQL Server 2008 server in a colo facility. I'm wondering if Server 2008 or Server 2008 R2 would be be better to use on these?
I would specify the latest version (including service pack) unless I had good reason not to.
Good reasons could include:
Starting with an older version is another form of technical debt, so only take it on if you need to. But be open about the possibility of needing to.