Bit geeky here, so apologies to the normals in the audience. A long term pain point with 64 bit version of windows has been the printer drivers. If 64 bit printer drivers even existed for the printer in question, fair chance they simply wouldn’t work properly. Beyond that, the vast majority of desktop systems are running 32 bit operating systems anyway, and the two simply would not meet. In my personal opinion this has been one of the fundamental reasons 64 bit OS’s haven’t gained much traction to date. So the thing is, moving forward with Windows Server, it’s all 64 bit. SBS 2008 is 64 bit only. Server 2008 R2 is 64 bit. It’s still going to be a rocky road, but here’s an excellent post from Susan with a few tips to ease the pain.

http://msmvps.com/blogs/bradley/archive/2009/11/23/migration-last-step-the-printers.aspx