For the teams that require umpires (10U and up), you should receive a check from the baseball/softball coordinator for your umpire fees during the regular season.
Example: The home team usually pays the $40 (more for the older 14U and 18U teams). With a 16 game season, there will be 8 home and 8 away games.
$40 times 8 home games = $320.
Any money remaining from home games that are not played may be used for playoff umpires or returned to the baseball/softball coordinator.
As for playoffs, since it happens quickly, it is only a few games and we do not know how may games each team will play: it is easier for the coaches to pay for the umpires up front and submit a request to the baseball/softball coordinator for reimbursement.