For someone confused about the questions you answer them very well (Thank you!). If the questions are vague I apologise. I have to disagree on them keeping anyone from clarifying the situations though. What has had me confused or just curious has changed with every post (as one thing is explained another becomes confusing/curious).
Your post pretty much verifies what I was saying then about the time frame and in what way it evens out. Examples of games are no longer needed. They where requested (and not just computer games mind you) for the purpose of determining the suitable time frame for a season/cycle, but seeing as you have already confirmed the intention is longer periods then that is no longer needed. The only questions that remain then concerns details like how long, how far up can you challenge, how often can you challenge, etc and that I think is not really needed to know in an alpha. Could even be said that it could not be known before knowing the approximate number of participants (since for evening out to happen takes longer time the more players are in a ladder).
Time it takes to climb the ladder will always depend only on the ladder size (and of course on your skill, but since that vary for each person it can be disregarded), the time the ladder has been running its cycle becomes irrelevant. I like this a lot, provided the cycle length is scaled properly to the number of participants.
When the time is there, I would propose putting these things (The general format as well as the details on cycle length, challenge frequency, etc) in the rules thread for the relevant ladder. Would be a shame to have to type out the answers all over again ^^
/Merf - Thinking new cycles are really only needed to prune away those inactive