DaasYochid,
“He’s making a simple point that we shouldn’t raise expectations unnecessarily. Not sure what you are reading into his statements that is bothering you so much.”
I think it’s the Catch-22. If a young woman is judged worthy of getting a date by her resume and picture, then of course she will do whatever she can to make the resume and picture stand out. Otherwise she might not get a date at all. But then we criticize her for raising a young man’s expectations and making him “feel cheated”? It’s a no-win situation. Demanding pictures is immodest, and one who does so is cheating himself. And if he has such picky preferences on appearance that he must see a picture before agreeing to a date, I’d consider that a huge red flag for shemiras einayim issues.