Most coaches should send cuts one to three times in the season. The first time is before walk-ons, and frees up roster space for the walk-ons. If you don't care about walk-ons (I don't), this is not necessary. The second set of cuts is the most critical, and is after walk-ons and before the first round of recruiting. This is what frees up roster space for the recruits. Since good teams rely on recruiting to get good players, having room for them on your roster is essential. Finally, if you are so inclined, you may cut the players that you don't think will ever play during their stay at your school after recruiting is over, although again I usually don't bother with this choice, except in football; instead I just don't play them and make the decision in the following offseason.