Looks like you might have been tagged because of your comment in that screenshot, haha. I'm happy that you were, though, because this discussion might not be happening without you.
This might be a bit more complicated implementation-wise (or maybe a flawed idea in general), but what if you could only submit games to jams if they were originally submitted to itch during the jam window? This would allow a single entry to be submitted to multiple jams (assuming all of those jams are open at the same time).
I think this issue is a tougher one to resolve than the free/paid issue, but I'm sure there's a solution that would at least be able to eliminate the really extreme cases.
Eric Neuhaus (@donkeyspaceman)
donkeyspaceman.itch.io