Agreed. No way, no how is Cushing the more respected physician. More famous in the lay public, sure, but I feel certain that even Dr-resurrected-Cushing himself would disavow the idea that he is a more competent or accomplished clinician than Dr-resurrected-Osler.
I think the biggest disappointment Osler would have with today's medicine is--as noted in other posts--the general "greed" (although that's a pretty pejorative word--let's say, "concern over compensation") of today's physicians. I think the young physicians/students of today don't realize that doctors really didn't make a great living until after WWII, when government assistance programs, ripe for billing abuse, provided enormous paydays for procedural specialties, thus paving the way for $multi-million cardiac surgeons, back surgeons, etc. Even today, I would be willing to bet that a major, if not the primary, unspoken reason that most students (AMG's, anyway) shy away from primary care (i.e., the kind of medicine practiced by Dr Osler and his colleagues) is the inferior compensation as compared with Ortho, Optho, ENT, Plastics, interventional Cards, etc etc; i.e., the pay-heavy procedural fields. And if you've ever gotten an Ortho turf for "diabetes management", you know that no one in Ortho is interested in practicing medicine the way Dr Osler did. This is largely because of the compensation, I would argue, although I'm sure 95% of the people in those fields would deny it up and down (and I'm sure many of them would be correct--but not all). (NB: I myself was considering ENT for quite a while, but in the end I've decided on IM because I'm just not ready to narrow the scope of my medical knowledge so early in my training (NB NB: Cards/GI is not for me either)) Obviously we need Orthos, ENTs, and so on, but in the time since Osler's day, the surgical/procedural subspecialties have mushroomed into being overserved in basically every city of any size, while general Internists appear to be a doomed species. I don't think Dr Osler would be very happy with that development.
Really though, it doesn't even have to be laid directly at the feet of the highly compensated specialties. Most pre-meds coming into medical school, I think, are expecting a life of high social status and reliably generous compensation, and that simply was not the case in 1800/early 1900's America. Dr Osler achieved an enormous degree of respect and the social graces of Baltimore, but this was because he was literally the tippity-top of medicine at that time, and dedicated his entire life to getting there. Most of the contemporary docs slogging it out in the small-to-medium size towns of the country were not in it for the cash, that's for certain.