#2 is very easy to answer; I don't think everyone is looking at the same model. I actually had a paragraph in my post about how sometimes in my art class someone would NOT draw the model at all, but would draw something out the window, or something elsewhere in the room. So indeed, it is not necessarily the case that someone else's portrait is actually a representation of the model. (And it's also not necessarily the case, even if they did try to draw the model, that their piece of art is a good one!)

#1 is harder to answer. On the one hand I agree with you that the main downfall of the analogy is that it assumes that G-d is just passively sitting around waiting to be understood, which is of course not my tradition's understanding of G-d. So I don't know that this is a less acceptable assessment of Judaism than of any other major world religion.

What "counter-intuitive elements" are you thinking of?