I've successfully used both Expression Offline 3.x and Obsession Offline 5.1, but not Obsession offline 5.2, 4.4.2, or 2.4.2, or ETCEdit. I have no doubt for all but Obsession Offline 5.2 it is due to the DOS nature of the apps, which doesn't seem surmountable with a program simply offering a windows API, but what do I know? I guess I have to stick with Boot Camp and VPC or VMWare's Fusion or Parallels Desktop for Win98se.
One thing I had to do to get the programs to find/use a USB floppy was to use the winecfg Control panel app to list/acknowledge the floppy drive (I never could get the floppy to show up as the A: or B: drive), then go to "~/Library/Application Support/Crossover/Bottles/name of folder with ETC application stuff in it/dosdevices", find the icon alias of the floppy drive (mine showed up as Untitled) and rename it "a/". Then my external USB floppy is seen and used as the A: drive for both Expression Offline and Obsession Offline.
If there is a way to do this in winecfg, I couldn't figure it out.
Joe Futral