I know I'm a little late to this thread, however, I would like to make a few comments based on experience.
First: Win95 will support larger than 6 gig harddrives. My guess is that your old computer's bios won't support the larger harddrives. You need to go to the harddrives webpage and download a bios patch to get the computer to see the larger harddrive. I don't mean to sound nasty, but your tech should have known this. This is how I got my old 233 running Win95B to see a 13.2 gig as 13.2 gigs.
Second: I had no problems moving UFT to my new computer running XP. I network the old and new machine together and moved files across. I loaded UFT 3.0 from the CD and then copied my old UFT 3.1 on top of the CD install. This got my root fonts moved correctly and covered my but regarding the Windows Registery (don't think UFT hits the registery).
However, I have no idea why UFT is not finding the roots font. So in case I'm coming across as a "Know It All" I'm really not. I'm just a guy "Armed with enough limited knowledge in a wide range of subjects to be dangerous.