Personally, I think a competitive specialty and/or academic medicine probably isn't a problem for a top OUWB student. They had three ortho matches in their first class (out of 47 graduating.) A MGH anesthesiology match, a Harvard Longwood psych match. Lots of strong Midwestern academic institutions. Granted, if you have a precise place in mind where you want/need/must go, a more prestigious/established school might count for something. But I saw a lot to be excited about in that inaugural match list.
The fact that WB has very strong ortho and optho departments (with research opportunities) probably counts for something too. Small class size presumably yields more opportunities, as well.