Also, regarding how the matches will be played (if there are more than one per round).....
I would suggest that the minimum to win (2 for best of three, 3 for best of five,etc, etc) be played in one sitting, then if there needs to be a tiebreaker(s) there is the option of scheduling that for another time.
Still need to know how these will be set up. Are they just going to all be set up and the two players sign in whenever they want (password protected), or will you have to have it each match set up by support before you can play? Think this still needs to be given some thought once the site is chosen (or as part of the selection process).....
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