The harsh reality is that, with only 57 teams, it's a small sample size mixed with some bad luck. I have played over 700 teams and my playoff win% is still ~25 points lower than my regular season win% (and ~80 points lower than my TOC win%). It happens

Some people build teams for the playoffs. You don't need as much stamina in the playoffs. Drafting an unbalanced team with a few cheap pitchers and backups you won't need in the playoffs leaves you more money to upgrade the players you'll use in the playoffs. If you can make it to the playoffs with those bums filling in. You'll do worse in the regular season, better in the playoffs, and possibly worse in TOC.
I don't draft this way much because the regular season is 8 weeks of fun and the playoffs is a few days of crapshoot. I enjoy the season more.

oz, thank you for relating your own experience and providing the reality check.

rbow923, thanks for the perspective. i have begun to think that way myself, as i really enjoy the regular season, managing my roster on a day-to-day basis and so on. as you say, the playoffs feel more like luck than skill.

Bumped up a short thread on this topic for you MJDoc.

The playoffs are the time to try taking advantage of every possible platoon/matchup/strategic advantage you can. Try to configure your pitching staff so your best pitchers throw the most innings and don't leave any bullets in the gun hoping to advance to the next round. If you need to burn Milacki in a Division Series Game 5, then do it. Of course there is luck (including bad luck) involved in short playoff series, but the best owners still win more often than they lose.