i am using vw2009 for some time now and Christian I think your strategy of upgrading one seat, evaluating, and then going for more licenses when the time is right seems very logical.
I do think both you and Brendan will be very happy with the interface improvement and improvements in 2D speed and stability. Let's not even talk about modeling here - we all have to ouput flat ol' 2D drawings to get our job done. I can attest that I have gotten several things done recently in about an hour that would have taken half a day in 2008 or earlier, if I could have done them at all. I'm talking complex polylines with thousands of holes, adding, subtracting, offsetting, etc. Simple things in 2009 have been the most valuable to me, primarily the Loupe, tool object highlighting, and grey others while in groups. It doesn't SOUND astounding...until you realize your drafting time is reduced by a significant margin.
Crashes happen, sure...but, eh... maybe some less than VW2008. And I have 2009 set to automatically save the last three backups at 26 minute intervals.
Cris Dopher