We play every Monday for 15 weeks, then have around a month off where we play just a few casual games and our big end of the season event - PokerMania. We aren't hardcore players, so we don't play for super high stakes (although we have started taking casino trips fairly often to play in events for fun). It's more about hanging out and having fun than winning money.
Monday night season games vary between 1x rebuy events ($30 T20k entry, one $20 T20k rebuy), deepstack events (same entry/rebuy but with T30k), knockout events ($10 from each buy-in to KO's) and a Secret KO event where there is an unknown bounty that gets half the pot (roughly $200-$250).
We give points based on finish, and pay out top 3 (9 and under people) or top 4 (10+ people) and have roughly 13-15 people a night. First is 10, 2nd 8, 3rd is 7, and so on through 8th which is 2 and 9th and below all get 1 point (for showing up basically). It's simple, and may not be the best, but it works for us. I've tried different methods and we pretty much end up with the same winners each time. We also only count a player's highest 10 finishes for the season championship.
Season winners get a bracelet (like the WSOP bracelet) and the top 4 finishers get an advantage at our end of the season event which is PokerMania. The top 4 season finishers get additional "blind chips". Everyone gets 1, but the top 4 finishers get more depending on where they finished - 1st gets 5 total, 2nd gets 4 total, 3rd is 3 total and 4th is 2 total then everyone else has one. The "blind chip" basically lets you play a hand on the big blind for free (although once things move past the blind, either raising pre-flop or action after the flop, then you have to bet that). We have had players use their blind chip the hand after being eliminated and stay alive before. It's an interesting wrinkle that has worked well.
PokerMania is a $50 buy-in with 2x $20 rebuys. Pots usually get a little over $1,000.
We also do specialty tournaments throughout the season:
+1 Poker Prize Fight - Players bring a guest to play in a showdown format (guest at one table and the club member at the other in the same seat) and the winner gets free entry into PokerMania (if the guest wins, then the member gets the entry). $30 buy-in with 2x $30 rebuys.
Money in the Bank - Our "week 0" event essentially. We play a normal 1x rebuy tournament but the winner gets a
"Money in the bank" chip that can be cashed in at any point in the season when the player wants to buy back in (before the money bubble so you can't rebuy in the final 2 or something like that). This can help you get more points and place in the money.
Valentines Day Couples Tag Team Tournament - Players are randomly paired up into couples, then each player gets their own T20k stack. Players choose before the hand which will play and the other sits to the side. Players have a "ask my partner" chip they can play once a level to ask their advice, otherwise the partner sits quietly and waits. When the game gets to the final two couples, they combine their chips and play as one.
March Madness KO Tournament - Pretty standard knockout tournament, just with unlimited rebuys while we watch the opening day of March Madness.
NFL Draft Crazy Pineapple Tournament - We did this based on Tua Tagovailoa because we are in Alabama and he's from Hawaii. Pineapple, get it?
Halloween Zombie Resurrection Tournament - $50 buy-in, that gets you T20k but when you go out, you are resurrected as a "zombie" with $10k in chips and you have to put one some piece of a costume we designate to show you're a zombie (like we made people wear fake mustaches or funny glasses). I kinda stole and simplified some ideas I saw here for this one, so thanks to whoever I stole it from lol.
Black Friday Team Tournament - The Iron Bowl is huge around here, so every Black Friday before the game, we make people draw cards randomly - red is Alabama, black is Auburn. Then we play a fairly standard tournament, but no one knows who is on what team. When the tournament is over, the winner gets half the pot and splits the other half with his teammates. So if you finish second and find out you aren't on the winner's team, you get nothing (or you could be last and be on the winner's team).
Dirty Santa Tournament - We play a Dirty Santa game where you bring a wrapped gift of around $30-$40 and as you go out, you pick a gift. Then when someone else goes out, they can steal yours or pick a new one. The first place person obviously gets the best gift.
We also do cash games, dealer's choice, and other fun stuff.