1 and 2) If in doubt, check the software requirements:
http://msdn.microsoft.com/en-us/library/ms143506.aspx[
^] they list the OS's that SQL Server 2014 supports. Versions of Windows Server 2008 are listed, but you may need to check the version and patch level.
3) Probably not, other than creating your database - which you can do in SSMS, Visual Studio, or programatically.