I don't think it was a dumb question, but moreso that there's no simple answer. There's a lot of controversy out there these days as to whether upsampling/oversampling actually improves performance or simply changes it. In addition, there are many different camps as to how the upsampling/oversampling is done that will give you different answers.
FWIW - I've been in one group situation where a DAC with oversampling capability was switchable was being demoed (apologies for not remembering which DAC it was)...out of 7 people in the room, 4 preferred the oversampled sound, 3 preferred the non-oversampled sound, and 1 heard differences but couldn't decide which he liked better....