One of the best posts about this topic was from @gemmintpokemon: When a buyer wants a PSA 10 within a PSA 10 - #2 by gemmintpokemon
The distinction between a pointed vs vague question. I had a psa 6 20th anniversary team rocket card. I had no idea why it was a 6, there must have been a subtle indent that I couldn’t detect. Since the buyer said they wanted to buy it and just confirm what they see in the scans is accurate, I ended up sending photos from multiple angles which sealed the deal.
Basically I am more accommodating to pointed questions. But the more common, “more pictures?”, or the worst, “in your opinion is this strong or weak” are just not even questions, they are traps. 