If you plan on making a playoff run and the player is important to that goal, waiting 1/8th of the season, while playing 9-10 games against divisional foes, is probably a bad idea. You'll have control of a player for 10 years. If he's a 23 y/o position player, he'll be declining when that time's up. Pitchers last a little longer but they also lose STM/DUR in their mid 30s.