When should people ask naive questions?
Perhaps you are overthinking the effect that asking questions has. Perhaps you are misjudging which questions are "naive". They don't sound naive to you, I think, but you worry that they are naive to others. 

I went to school long ago - mathematics. Before the internet. Before personal (or many) computers. But my solution to having a question was to ask it. I asked a lot of questions. I didn't bother people in their offices for simple(ish) things, but in class I pretty much always had my hand up. My mother was often exasperated with me for asking so many questions as a child, but I never got that sense that my professors were. 

But the effect was that almost everyone thought I was very smart. Smarter, probably, than I really am. It turns out that I was just bold enough to ask the questions that other students were afraid to ask. Some of the questions I asked, of course, were the result of errors made by the prof in lecture and he/she would then correct them, but most were just gaps. 

But the best answer isn't always a direct answer, but a hint as to how/where the answer can be found. The simple answer doesn't usually give the context you need. The "answer to life, the universe, and everything is 42" may be correct or not, but it isn't enlightening. It is the connections between things that are important, everywhere, but especially in mathematics. 

Some may think that you are asking things you "should" already know, but everyone will see you as engaged, rather than complacent. 

It turns out that, just as in a course, in grad school you probably aren't there to prove to people that you don't need to be there. Ask and ye shall receive.