Meh. I know a guy with a very average job and looks like Groucho Marx and Randy Quaid had a kid, but who continues to date exclusively model types, best I can tell, totally based on his personality. One recent girlfriend said she found him attractive because his look was so "interesting". And we ALL know guys like this. And see them at the bars, restaurants, beaches. It's so common it's almost cliche. That you haven't seen this phenomenon is somewhat remarkable to me. As mentioned a whole industry exists of homely people selling books and videos of how to pick up attractive women, through personality, humor, etc. Lots of attractive people have unconventional views of beauty, or hangups, daddy issues, whatever, too, which drives them to date "down". Probable outnumber the people with purely conventional magazine cover instilled views of what's attractive.
Romantic endeavors are really not about "logic" or "common sense"and that's, I think where your train flies off the track. And that's, I think, where OPs notion that once he has more trappings of success by being a med student, doors will open. But he's wrong for much the same "logic" reasons you are. Show me a guy who is the life of the party, knows how to talk to women, exhudes confidence and I'll show you the guy whose going to date well above his league. Show me the guy who didn't get dates in college and hopes to turn things around in med school and I'm betting he will have plenty of time for studying.