Could it be that medicine was more individually "caring" before the introduction of highly-codified procedural standards and allopathic/evidence-based medicine?
A personal anecdote: I've had a tremendously hard time finding an ophthalmologist to treat a chronic and very annoying type of allergic conjunctivitis. I finally just found a great doctor — an "Osler type." She actually took the time to try to diagnose the issue, walk through my medical history with me, and focus on figuring out the root cause. All the other ophthalmologists I've been to have just put me on steroidal eye drops after running through a checklist.
I've seen this same thing in other parts of my life too. I had a period of about two years when I was a (younger) teenager where 3 psychiatrists and one GP diagnosed me with depression, anxiety, ADHD, narcissistic personality disorder, Bipolar I disorder, Bipolar II disorder, and more.
I finally got off the treadmill of medications and completely unfounded diagnoses, took a few psychedelic trips, and left home to travel alone for a month. On a follow-up visit my psychiatrist was stunned to learn I was leading a successful life without medication. (He had previously told me that "people with your kind of depression almost always need SSRIs for life.")
If only more doctors had the empathy and courage to wean themselves from the checklist style of medicine and practice medicine in the way Osler emphasizes here — by preparing their souls to do so.
I think there are "House, M.D."-style situations where the checklist will kill your patient and a quick hunch will save it. But the usual doctor's visit because of an itchy eye isn't.
As an IT professional, just think of the number of times where it really was one of point 1, 2 or 3 on the checklist: "is it switched on?" "is it plugged in?" "have you tried turning it off and on again?". Of course those are often useless. But when they are not they do waste far more time than just quickly checking...