Its not even about if its too much work. I'm very skeptical as to how many players would actually take an active roll in participating in something like this or reporting their wins and what not.
How about something like a month long tournament? For instance we could begin it on the 1st Sunday of every month. You guys can have 1 week to face your respective opponents. Here is an example of how the bracket would look,
After 1 week anyone that doesn't finish playing there opponent will either be moved up or auto Dq'ed