@bcopeland, small possible interface issue with the file manager. I uploaded some of Zooz's crazy long filenamed OTZ files today, and noted that no matter which orientation I held my tablet in, nor which browser I used, the trash can icon didn't appear on the lines with crazy long filenames.
I haven't booted the PC to check if more screen real estate works around the issue, but perhaps placing the trash can icon/link first on each line in the file list might address the issue with long filenames? Assuming others can see the same issue that is!
S.