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 ...