The long file name error refers to the entire path name, including folder names. If that whole string exceeds 255 characters, it's too long. I'm guessing that in the copying process you added a folder at the top of the directory tree that pushed it over the limit - maybe just by one or two characters.
Checking the obvious - make sure the drive is formatted with NTFS. If it's in FAT32 or some such, it'll max out when the FAT table gets full, whether or not the drive is full.
I've had good luck with both Western Digital and Seagate, less with Toshiba, and have about a half-dozen 1gb and 2gb units running right now. Intersting that the Toshiba laptop I'm using now came with a Seagate hard drive, not one of Toshiba's own.
If all those drives have failed on the same USB I/O card or hub, I'd get a new card or hub by a different manufacturer.
al
Fulltiming since Apr 2007 in 2000 Rexhall Aerbus, towing 2012 Honda CRV. 47 of the lower 48 so far.