21 weeks.
You could easily do two 10 week halves with one week at the end for playoff/team sweeper?
Regarding money, take the total amount you expect to have. Subtract any special awards such as first place, second place, high series, etc., then take the total points available for the season and divide it into the remainder of the cash to create "point money" that can be divided to each team based on amount of wins. In other words, each point will have a dollar value. Money can be available for the sweeper for high team games, high series, high individual game, series, etc...
You can jumble the numbers and create option 2 and option 3. It's not very complex once you start at the "end" and work backwards til the money is gone.