While sometimes it seems topsy-turvy that we understand this issue better than Pediatricians and Family Practitioners, it is important to remember the legacy of doing it wrong that even modern doctors have to grapple with.
I remember vividly a story a friend told me about a group of young doctors sitting through a presentation on well-baby checkups. The presenter, who I believe was a senior Ped, stressed that the baby's foreskin should not be retracted. Ever.
One of the recently-minted male docs in the front row just blurted out, "But... but... that's completely counter-intuitive! How do you clean it and check it?" He was told to sit patiently through the rest of the lecture about the development and functions of the foreskin, and he would soon understand.
They were lucky they had an experienced old hand to explain it. Too many doctors of prior generations honestly did not understand intact anatomy and did just awful things to boys -- probably a primary contributor to all the horror stories we've heard from men who were cut in childhood.
Just today (today!) this comment appeared in the NYTimes from a retired surgeon. [I don't believe this is copyrighted material; it is not authored by the paper, but I shortened it anyway.] Can you honestly believe a doctor not knowing whether his 3 eldest sons are circumcised?!? And his beliefs about the foreskin!
I have three middle-aged sons... I can’t remember if they were circumcised, but presumably not. I also have [by my current wife] a young adult son who is not circumcised. At birth he had an adherent foreskin which is treated by forcibly separating the attachment, removing the trapped white smegma and maintaining the release at bathing times. However, his birth occurred during the period of rising wrath over pedophilia and his mother was a very critical person. So, I was just afraid to maintain the necessary retraction during bathing and don’t know what the outcome was. I do know it required no other medical attention.
My stomach flipped over a couple of times when I read that, but that's honestly what nearly the entire US medical profession believed at one time. Unfortunately, the medical profession is as susceptible to hand-me-down information as any of us are, and some things change slowly. But I believe that if American doctors weren't so reluctant about understanding the foreskin, knowledge in this area could advance rapidly.
I think I understand a Ped saying she just wants to check for pinhole opening; that's the only reason she would retract without reaching the glans. But "pinhole" is rather uncommon and has no fixed definition anyway... and most importantly, it resolves itself just fine in 99.9% of cases. We all know painless ballooning is benign, even if not all doctors got the memo.
I reiterate my rule of thumb: everything having to do with the penis moves in the direction of the urine flow. Wiping to clean, keeping an eye on smegma pearls, and even not freaking when DS occasionally pulls his foreskin forward like it's taffy. (It relieves itch, helps the breakdown process and feels awesome.)
When he's ready to try the other direction, he will.