Four owners won the World Series with their only playoff team...
boozerep (31 pts)
neabaseball (31 pts)
oskies (31 pts)
thejuice6 (31 pts)
Among those owners with two or more playoff teams, here were the teams that averaged the most bonus points per playoff team (the avg was 13.6)
jetscanes (2 teams, 28.0 pts per team)
Yaz_Benders (2 teams, 25.0 pts)
schwarze (3 teams, 23.0 pts)
bigmc (5 teams, 22.6 pts)
ctorkelson (2 teams, 22.0 pts)
markeking (3 teams, 21.0 pts)
msleath (3 teams, 20.7 pts)
covman2003 (2 teams, 20.0 pts)
And here are the teams with at least 500 regular season wins with 2+ playoff teams that average the least bonus points per playoff team (in other words, their lack of playoff success killed their shot at advancing to round 2, if they were on the bubble)
wportal (523 wins, 3 teams, 6.0 pts per team)
cstrohmier (534 wins, 2 teams, 6.0 pts)
wildthings1 (575 wins, 5 teams, 7.4 pts) --> dropped from 1 to 4 overall
footballmm11 (505 wins, 3 teams, 8.0 pts)
bigfatjew (515 wins, 3 teams, 8.0 pts)
Area51man (515 wins, 4 teams, 8.3 pts)
jfranco77 (517 wins, 4 teams, 8.8 pts)
stroh23 (522 wins, 3 teams, 9.0 wpts)