Yes for the oldest played. I don't really know how many resets it takes, it all depends on the words (how much questions you've answered before) and the size of the list.
I don't really get your last paragraph, but the admins don't allow automating or cheating in any way, you must be careful about that if you try to use an automating software, even if it's to reset the list. Maybe I haven't understood your point clearly in that final paragraph, if so, could you please explain it again? ;)