I'm not sure if you're still looking for an answer. My apologies that you haven't gotten one until now.
The "skip" checkbox should be under your control. If you don't expect that someone already exists on WikiTree, you don't need to skip them. If you do think they're already on WikiTree, you should skip them regardless of whether our system finds the match. Our matching system is very conservative so as to not overwhelm you (most already feel overwhelmed by the matching/skipping).