Yes, always try to make the playoffs (a bird in the hand is worth two in the bush).
I just "won" my division in Moneyball during what I anticipated would be an off-year. It was, as I finished 74-84, but the next closest guy finished 74-88, and my team of rookies, declining veterans and temporary stopgaps went on a run that ended with a World Series loss. That earned me a free season, and it was lots of fun. There's no guarantee that your future superteam will make the playoffs, because you could have injuries or your division mates will improve even more. Always go for it while you can.