Doug Kurtis did 76 sub-2:20's.
http://www.lelingweb.com/pro/hsr6/kurtis.php
From that, one might think there must be a bunch of people to have done what you mention. Somehow I don't think so. Kurtis was/is really a remarkable athlete.
The people who managed three or four sub-2:50's per year, back in the early 80's when Boston required sub-2:50 to get in, probably (I am just conjecturing here) did not keep up that standard for a long enough time.
Doing it twice a year would not have been enough. Most people are not going to be able to maintain that standard for 25 years.
Someone like Beardsley, who would have an elite career with 20 or so races well under 2:50, then returned to a good fitness level while still under 50 years old, might be the type of person who would have a good shot.
Come to think of it I'm not sure if even Rodgers achieved this. I would guess he came very close if he didn't.
If I had to guess I would say that there are fewer than 50 people who have done it, ever.