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The election pool has been pretty much a closed community for the last 4 cycles, no additions or turnover. Sixteen is the ideal number because we do some things, similar to the NFL, in which contestants are placed in "divisions" or "conferences" and compete against each other there in addition to the group as a whole.
We pick each senate race, gov race, selected house races, and in presidential years every state result. You pick the winner, the percentage and the net result. The competitive races are the most crucial because picking the wrong winner is severely penalized. There are pools and payoffs for each (house, senate, gov, presidential) as well as an overall title. We tweak the specifics every cycle based on past problems, not unlike the BCS college football mess.
Overwhelmingly these guys are middleaged and conservative. They gleefully allowed me in as a surefire lefty pigeon prior to '96. I did gobs of creative state research, using handicaps similar to sports pointspreads to amend poll numbers, and cleaned their clocks in both '96 and '98, winning the all-around and virtually everything else both times. Then I blabbed about my methods, like a stone moron, and many of them caught up. Still, in 2000 I would have placed first again, and not 3rd, if Gore had rightfully prevailed. Last year I dropped to 6th, mostly because of some blown gov calls. I got the senate almost perfect but so did nearly everyone else. Those so-called senate upsets were all in Republican states, other than the Minnesota mess, and virtually no one in the pool ignored that.
You might try to get your own pool going, for fun or cash, maybe with other DUers. The limited races this year would be a good test run.
As far as the offshore betting, you need to get an account with one of the big and reputable outfits that primarily deal with sports wagering but throw in politics as an aside, or use the account of someone who is already in. It is convenient, but the money is forwarded ahead of time to give you a balance. The ones that deal politics can vary. "Cris" and "Olympic" are huge and not likely to screw you. I lost a chunk of cash in 2002 when a golf-oriented site, betcarousel.com, went under in March right after I made a substantial deposit.
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