If the flight is under 500 miles, I would rather rough it in Y than pay $50.
I did not get upgraded on the DTW-DCA flight on a Tuesday morning (10 a.m.) flight. I was 2nd on 4 seats when I checked in on line night before, and then I was 1st on two vacant seats, but didn't make it. I had never missed an upgrade between DCA and DTW over the last 12 years,