To begin, the member must be extremely unlucky to have not reached Legendary in this time. I'm sure that some members here had that quality, however they did not have the next or did not remain active enough to reach it.
Secondly, the account must have a significant amount of potential activity. This means that not enough posts were made in a large number of activity periods (I.E their post count is less than or equal to their activity) allowing them to upgrade their activity as they post.
If this is the case, the member will be able to post directly up to their Legendary quota without it being skipped over by a full activity period (As seen with Lincoln6Echo).
That's pretty good logic that's over looked. Instead of having one chance out of 14 days, you get one chance to every time you post. So it does place those prolific posters like the OP at a disadvantage.