I have been running Visual Studio 2005 on a Windows 2003 Server VM for the last few years and I just got a Visual Studio Professional with MSDN Professional subscription ($300 off!).
I plan to setup a Windows 2008 Server VM to do my primary development on and I was wondering whether I should get Visual Studio 2008, or because I've never used it, skip ahead to the 2010 beta?
Edit
In VS 2005 I primarily use C# and basic web forms ASP.net. I'm hoping to start upgrading some of those projects but may have to hold back if other people who I collaborate with don't upgrade.