My upgrade from X1/xp32bit to X2/win7 was pretty manageable and I think a fairly low risk one
My son gave me a 128Gig Solid Solid State Drive and a copy of Win7 for Christmas
I went dual boot (8 gig of memory on an Asus MB) and a EMU1212m card
The dual boot was pretty painless and getting the soundcard up in both OS's was okay
Then I bought the X2 Producer download and installed it in 64 bit on Win 7
But the big thing is to go slowly on getting the plugins up - pretty much install the whole Sonar X2 and then pick off the plugins one by one. Not sure if this is everyone's cup of tea but it kept my stress level down.
With the SSD drive this thing loads REALLY fast - and between the Breverb and 64 bit OS this thing never is breathing hard and that's a really good feeling.