If you click on a tag, you get a list of questions using that tag. Before applying the tag, ask yourself the following question:
Would I expect to see this question in a list of questions using this tag?
For example, I removed the "grades" tag which you applied to What, if any, roads are open to graduate schools for athletes with borderline grades? because the question is not about "grades" and "grading." I would not expect to see such a question come up in that context. I would expect to see it in a question about graduate admissions. I might also expect to see it in a list of questions about athletics.
However, don't tag or retag a question if you're not certain if a tag should apply. It's better not to edit tags, particularly on old questions, if you're not positive the tags you're adding are relevant. If you think something needs new tags, then you could suggest it as a comment instead of retagging.