I'd 'punt' spending that kind of $$$ on fantasy sports...too many other expen$ive hobbies (e.g. guitars, 6 year old...) that eat money to bother w/ that.
That way, if my $10 office league comes down to rooting for say a Cardinal SP or something horrible like that, I can root for the Cubs to smack his butt. Or, ideally, him to pitch 8 innings, give up 2 unearned runs and strike out 12 Cubs while my RP vultures a win somewhere off the beaten path. Once I start looking at math, I can always come up w/ some sort of unlikely math that leads to a W for me both ways but IRL would trump fantasy in the unlikely event that the Cubs would be that close to the wire at the same time my fantasy team would be.