*shrug* I have been able to successfully upload everything I put up there. I uploaded a zipfile full of music that weighed in at ~3gb last night. I deleted it shortly after for legal reasons, but yeah it uploaded fine for me. It even capped out my upload speed, which was quite nice.
This is a text file made and uploaded by sully.
Nevermind, I think I found the answer. I made a small change to the file and uploaded it again and the download link I got was http://www.filedropper.com/fitestest_1I suppose the numbering at the end will continue to increment the more copies of the same filename are uploaded, though I'd still like to see someone else upload to see if the numbering persists across users. Also, the link changed, but the filename did not. When I downloaded the second one, it still presented itself as fitestest.txt.
You can't complain about the 7 day trial. They give you 50gb for free for 7 days.