It wasn't so much the time as it was the reported size of the data. Something like 30GB or something when the game is only 4GB.
I was like 'WTF?!' and hit cancel.
It wasn't til later that evening that I realized the drive was corrupted.
After that, I got another drive (60GB) that already had a few PS2 games on it, and put that in a USB enclosure and went from HDD to HDD to copy GTA:SA.
I got an error a couple minutes in. Putting the 60GB drive back in the PS2 resulted in the 'No Games are Currently Installed' message. I then ripped Sly Cooper to the drive. Everything was going fine. Once it was done, I got the same 'No Games are Currently Installed' message.
Basically, I need to reformat it and start all over.
That's the extent of my WinHIIP horror stories. Great software otherwise, but there are bugs clearly. Dangerous ones at that.