Mathematical Chance of Winning Your Series, Explained
Your likelihood of winning a series can be calculated using your likelihood of winning a single game, assuming it is constant, and ignoring other factors.
For a three-game series (assuming all three games could be played), there are 8 possible outcomes.
WWW WWL WLW LWW WLL LWL LLW LLL
The probability of each of these outcomes can be determined, and the outcomes that have at least two wins can be added together to obtain your total probability of winning the series.
A five-game series uses the same methodology, but has 32 possible outcomes. I shall not list them here. See the linked spreadsheet.
Furthermore, the probability can also be determined if you have already failed your series attempt (while getting at least one win), to include your "free win" that you get on your next attempt. It turns out that you are dramatically more likely to succeed on such a series attempt.
So... if you would like to see your chances, check out the linked spreadsheet. If I set the permissions correctly, anyone should be able to use it. If you have trouble, let me know. Also, try copying it to your own Google Docs and see if that works.
It is my hope that seeing some actual data will remove some of the mystery that there seems to be so much of, regarding succeeding in your series.
Thanks guys and I hope you find it interesting.