To me, winning a deep league takes knowledge, skill and strategy with a little bit of luck thrown in. Shallow leagues are mostly luck. JMO.
I'm in a 13 team, 37 man roster league(23 starters/14 farm). Going in I knew OF was shallow this year, that didn't stop me from waiting too long to fill in my last OF spots like a moron... and now I'm stuck with Murton, Nelson Cruz and Delucci to fill two spots. Luckily I have the deepest, best (IMO) pitching staff in the league from which to trade to upgrade my OF spots (Oswalt, Peavy, Smoltz, Hamels, Maine, C. James, Davies, Garland, Byrd and Pedro Martinez stashed until the couple of months).