I know it seems very important, but I'm starting to feel that it doesn't matter as much as the concern expressed on this board. I agree that the training varies, but this field involves a lot of self study, so if you are at a place this is 'low-tier' you can make up a lot of the deficiencies on your own, I think. WSU/DMC is somewhat lower tier, and two years ago they sent a guy to UFlorida. A former chair at Mayo Scottsdale went to Howard for residency. These are just a few anecdotes, but people from 'low-tier' programs are getting jobs. It may be difficult to get the exact location you want, but you should be able to get a job in a region of your choice.
I think as far as trends of certain programs sending graduates to academic jobs vs. private practice has a lot to do with the individuals. Someone who ends up at Pitt or Loyola just intrinsically is more likely to take a private practice job compared to someone who does their training at Penn or UCSF. It's really hard to get a handle on this because the n=1-5, so it's hard to say whether a program has a hard time finding their graduates ideal jobs.
As a person who didn't match initially, I felt strongly and still feel that landing a spot is the hard part. Afterwards, it gets somewhat easier. When I interviewed at the 20 or so programs the last two years, none of the seniors seemed concerned about finding a job. The one concern is that at the weakest programs, there may be some deficiencies if you want to specialize in a specific area (i.e. peds, brachy, SRS) and you may need a fellowship. So, the year you save by matching at a 'low-tier' program may be made up by having to do a fellowship. Not sure how accurate this statement is, though.
-S