Interesting thread, particularly like polyglot's first post.
I'm on the verge of stepping into portraiture with a bit of freelancing in mind, and with much trepidation - perhaps partly because I'll be shooting digital primarily. I'm also surprised how many professionals are clearly doing very well without any sense of composition and in a lot of cases, very poor aesthetic judgement in post-processing. The thing is, clients are obviously happy with the results and with business in mind, any sudden self-awareness (in reference to Dunning-Kruger effect) might leave them struggling to pay the bills. Being as competitive as the game is, anyone with creative drive might ask themselves "why bother trying so hard?". A strong mind for business seems to be much more advantageous - is business 'vision' art? People who champion Apple seem to think so.
There are a few videos on YouTube by a successful photographer, Zack Arias. His insights are very informative, but I have to say, despite his criticism of many in his profession, his own work is pretty middle of the road. But perhaps I've spent too much time as an amateur aesthete. A big reason for my wanting to get into portraiture is the work of David Eustace which is so classic, simple and unaffected and about a million times more artful (I didn't say 'better') than Zack Arias. See his 'Character Project'. He started in his early 30s, after working as a prison warden in Glasgow! Surprising how many people get into professional portraiture as a dramatic and sudden career change. This seems to be getting more common with entrepreneurship becoming so celebrated in the current economy.
Without seeing the portraits you mention it is rertty impossible to give an intelligent answer. However I worked for the world's largest news gathering organization, a major univerisity and have photographed celebs from Elvis to the Beatles to Gomer Pyle. One of the skills needed in taking portrature is to overcome "bigshotitis" -- the syndrome where Mr. Big is too busy to give the photog the time he needs. I read about one photog who was told he was going to be ushered into the Big Man's office and would be expected to shoot a photo and get out ther in a couple of minutes. He negotiated enough time before he shot the photo to "change his film." He used the time to size up the room, the guy, the setting and so on. Pretty ridiculous. I assume the photos you viewed were done more-or-less in the fashion of the time, but perhaps badly. I like decent coffee but it is almost impossible to get a decent cup anywhere, including at StarWeGotYerBucks. That's the world we live in. No point in blaming Gigetal-Digital for everything.