To answer your question CR, I took a look at my stats and the fiirst thing that jumped to my attention is that I will have been playing WIS for 9 years as of Oct. 7th. Doesn't seem that long.
Anyway, for about half that time I've basically only been playing three leagues, two specifically I've been in for a while... a prog and futurekid6's twist league... and the third varied, but has been a prog for the last 5 seasons. So, from 194 total teams, I have 103 playoff appearances (53%)... of those playoff teams 34 made the finals (33%)... and of the final teams 15 (44%) won the WS and 2 (13.3%) won the ToC (neither of the ToC winners were prog teams).