From an Owner Rating standpoint, assuming wins and losses even out (and I don't think win points are more than loss points), if you make the playoffs 1/4 of the time, the WS 1/16 of the time, and win the WS 1/32 of the time, you'd average 5.8333 points per season.  You start with 1400 points, so I guess my rating should be 2765 instead of 18,377.  However, even though I win only 52% of the time that translates to over 1500 more wins than losses, and each game is worth anywhere from 6 to 10 points.

I can't believe I'm debaing my own mediocrity ...

Here's a great candidate: cbaltz_ca in a league that just finished named his team Yearning for Mediocrity, and compiled a perfect 81-81 record. Furthermore, in two years on WIS with 57 teams, he has a .511 winning percentage and one championship. Owner rating: 4004.