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Why is there a Deadline for the Playoffs?

It seems silly.  There is no season after the playoffs, so why does each round need to be played by a certain date? 
 
In the early days of the league, there was no deadline.  For the most part this worked well because it allowed for maximum participation.  Over time, however, we encountered more and more problems.  One third of the playoff matches were getting played after September 1st because it was becoming more and more difficult to accommodate everyone's vacation schedules. 
Sometimes, this would extend out even further.   True example: Women's doubles semi-final.  One side played in early August and was ready for the final.  The other side was delayed, first for vacation, then for injury, then for vacation, then delayed again for injury and various other scheduling difficulties.  By the time the final played it was late October.  One of the players on the other team in the final played only in this league in the summer, so she hadn't played a match since early August.
Half the players in the league would let it extend endlessly to get the matches in.  The other half really do not want to be playing matches from a summer league past the end of August.  We do our best to allow for maximum participation while accommodating both points of view.
Many times players are only away for the first two weeks of August.  Since they are here for the last two weeks to get in their playoff matches, they believe they are all set.  This real life example happens at least once a summer, and most years at least 2-3 times.
Doubles Semi-Final:  Team 1 - Unavailable until August 15th.   Team 2 - Unavailable August 14th - 21st.
So why no just play the semi-final on August 22nd?  You still have another week to schedule the final.  Ah, but it's a semi-final, which means there is another side.  And on the other side, guess what?  They are available to play the semi-finals right away in early August.  After that, they are here all the way until August 22nd to play the final.  After that, however, they can't play until September 4th.  That should be no problem.  If they have already played their semi-final on August 7th, they have two weeks to get in the final!   Now, however, they would have to wait until after September 4th to play, nearly a month since they last played a match.  And what if someone from the first team is not available from September 4th -11th? 
 
That, in a nutshell, is the problem we face every season with multiple divisions.