People naturally tend to confuse the map and the territory, even when thinking directly about the territory. Thinking explicitly about the map requires a second-order map, and that just makes things even harder.

I would consider it a bug.

(Note that I am interpreting your phrase "questions about the 'meaning of math'" in a particular way, as "questions about the physical significance of specific mathematical facts and constructs". I chose this interpretation based on some of your previous comments, which suggested that you weren't yet totally on board with formalism. If, however, you instead meant "questions such as the one whose answer is 'mathematics is the map, physics is the territory'", then those questions are perfectly meaningful, and there is no reason your mind shouldn't consider them such.)