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Looking at the Entity Framework 5 release, it has some nifty features I'd like to take advantage of (e.g., automatic query compilation, proper lookups of indexed varchar columns). However, many of those features will not work unless you have .Net 4.5, and we have .Net 4.
So, we just need to install .Net 4.5. However, .Net 4.5 doesn't work on Windows Server 2003, which is what our development server is on. So, we need to upgrade Windows.
And once we upgrade Windows, .Net, and Entity Framework, there are still some features we can't take advantage of (e.g., table-valued parameters), because we are on SQL Server 2005. We were supposed to upgrade to 2008 months ago, but it never happened. So, that will need to be kick-started too.
This could take a while to get all these ducks in a row...
Funny thing is we already have licenses. We just need the personnel to perform the upgrades. I'm just a web monkey; they don't (usually) let me install stuff on the servers. They already have plenty of DBA's, software engineers, and license managers to avoid installs as long as possible.