When listing an item it keeps saying "Please reupload your files"
Slow down buddy-o!
This happens when you are uploading files too quickly.
Slow down!
....
Take a breathe....
...chill and wait for the first file to be uploaded and then upload the next file.
File names
Also make sure your file names don't have weird characters - no japanese/chinese/other languages in the file names. Don't include a lot of periods or random characters.
BAD FILE NAME:
Horrible file name, will probably break our servers. Don't do this.