If there is anyone out there who can help me learn to coach in the playoffs, I am longing to talk to you.

I rarely don't have a bye in the one world I am playing in. Yet, in 8 years of that, I have only won two playoff series and have never advanced to the World Series.

Clearly, there is something I just don't understand about the game. Would love thoughts of those that understand this game better than me.

A lot of owners think the playoffs are a bit of a crapshoot.   Especially the 5 game series.

A few things you might be overlooking:

1.  Roster composition.   You need less pitching.   Short series/off days.   I carry 8-9.  Some people think that's too few but I don't have problems.   Don't carry anyone you don't want to pitch.  You can probably get by with three starters.   That means SP4/5 can move to LRA.   LRB/SUB aren't needed.  Carry specialty players instead.
2.  Turn off rest.  They can rest when the playoffs are over.
3.  Tighten up pull ratings.   One bad game can mean the end of a series.  Plus, if it's your ace getting pounded, getting him out early might mean he can pitch earlier in the rotation again.
4.  You can "gameplan" a little more.   Weak C on the other team?  Crank up SB attempts.   They can't hit lefties well?  Carry more lefties.   Heavy platoon team?  Start LH, load RH in the LRA/SUA slots.   

I'll help you Dubs. 


Oh that's right.....I suck too!  Doh!

Is there any setting that prevents all your best players from going in the tank in the post season? That seems to be my issue.

Nope.  My regular season ace seems to have a 9+ ERA in post-season every year.