The best way to have head to head battles is to have some early SS games and some EM games. They are much more fun on multiplayer games than DMD games are because of the ball times. Four people can play Sinbad and all stay riveted to watching eachother's play too because the game is wild and ball times are short. It is fun to watch the game screw the other players and your friends can also laugh as you get screwed.

Yeah, I have several 2 and 4 player EMS with two inch flippers and they are the best games for competition. The newer ones can have way too long of ball times to keep everybody interested. We compete almost every night on most of them and use the single player games as fluffers while waiting a turn which usually isn't very long. It is a lot of fun.

My wife, stepdaughter, and I do this all the time. We play every game in my collection and do the 3,2,1 scoring system. My stepdaughter has a scoring goal for each game. If she reaches it, she automatically wins.

(Your poll doesn't really have a response that fits me but...)

Once or twice every winter I have a pinball and vid game throw down in my basement bar and invite mostly work colleagues and spouses from current and past jobs. Many are already predisposed to liking pinball or arcade games, but they are casual or beginners in pins compared to me. I have free play for a couple hours then a very beginner friendly tournament with good prizes. I've learned a lot about how to make it accessible and fun if anyone's trying to do something similar.

Jack

I will usually run some sort of tournemant if there are at least 3-4 people over. From Tommy dollars to quick brackets I think doing some competitive stuff just raises the bar. I will also run 1 ball tournaments on games like BSD or AFM which are a quick way to roll through a tourney. BSD is fun because Mist is qualified and everyone is struggling for that one shot.

I'm not sure you would call it casual... We are pretty competitive here so most of these type tourneys are winner take all... Hubby and I have "tournaments" on our pins all the time (we won't discuss "prizes" ) pretty much every weekend we pick a bank of games and play best 3 of 5 or 5 of 7.
Over the Holidays, or when the kids are here, we have matches with them on pins and we get out the old WII bowling for matches. My Mom even joins in for the bowling. And we can't forget to drag out the good old Gamecube for a couple rounds of Mario Party or Mario Cart...(no prizes involved unless you count kicking Mom and Dad's butts at something!)
We have pinball parties here also and invite friends, we have food and beverages, and lots of trash talk and competitions (but our group is so big at this point that some in our Cincy Pinball Group (80+) don't have the space to have an open invite, so we have started a league (we had to cap it at 30 for space etc.))...usually after the league dates there is some $1 games or matches for fun, but someone usually goes home short some $1s.

Phoebe

I would love to find out more about this. We have a growing number of pinheads in my area and a few of us have 8+ pins in our collection. We are kicking the idea of starting something but not really sure how to do it as none of us have ever participated in a tourney or competition.

Casual players don't want to get their ass kicked on a game that the owner of can stand there and play a 20 minute ball on. They lose enthusiasm fast that way. That is why even though I have a lot of practice on the older games, newcomers pick up on them fast and scores on those games are never that high anyway. And after a short while of practice they can start to win.

Put 2" flippers on every game, problem solved.

When I put them on my Dredd, it did shorten ball times a bit.