[dcasper70]

I play in a 'League' type game that has done this rather effectively.

Typically, we play every 2-3 weeks or so, and get an average of 23 players (min this year was 14, max was 36). We play 2 $40 buy in tourneys each night, and 5% is put into a side pool for the end of year 'Finals'.
The point system is based on # of payouts, so if top 5 get paid, winner gets 5 points, 2nd - 4, 3rd - 3, etc. Winner also gets 1 bonus point for, well, winning...
At the end of the season, the top 10 in points plays for the side pool, no buy in.

This year's pool is $2300. I'm 10th! [img]/images/graemlins/laugh.gif[/img]

Alternative thoughts we've had.
Points awarded based on # of players. Twenty players: 1st - 20 (+1) points, 2nd - 19, 3rd - 18, ... 20th - 1 point.
Points translate into extra starting chips for the Finals.
Players not qualifying for Finals can buy in for equivalent seat value + $50 (if Finals is $2300, seat value is $230, outsiders can buy in for $280).
Must have played a minimum # of tourneys to qualify.

I suggest you just pick a system and do it. Start with a shorter season, say 4 - 6 months depending on how often you play. Over the course of a season you'll get planty of input as to what your crew likes, and you can adjust it for the following season.

The action gets crazy towards the end of the year. People on or near the bubble can't miss a week in fear of getting bumped. Lots of added pressure makes for very interesting evenings!

Good luck!