From the looks of it, the problem is this: Harry was hitting Load Online League File to download the new league file. When it finished downloading the league file and updating, it wasn't updating the date in the game (although the date in the reports were updating)... so Harry hit Continue and it took him to my team, which he was able to release a player, submit and export and overwrite my export.
So, a couple things seem to be needed:
--The ability to select anything in the Import/Export menu on the team page should only be available to a team with a manager who is signed it OR the commish. The items should be grayed out or the menu not available for everyone else.
--The ability to use the Continue button should only be available to the Commish. The only real benefit it gives the team is to sim ahead, which is questionable in value, but generally frowned upon in the online world.
--Finally, after loading a new file with the Load Online League File option, maybe automatically request that a team logs in again to refresh the league date? I personally haven't seen the league date not update, only because I am controlling everything as Commish, but it has happened to Harry 3 times in a row now, so I have to think something is up.