Top notch picks for various sports: http://www.professionalhandicapping.net - this is a pretty impressive handicapper. They have 67.46% winning record (85 wins - 41 losses), and they charge $50 per month, which is great!
http://www.goldkeygames.com/ Their website is extremely hard to navigate and they post too many of their old picks on the site.
BUT, they steady produce winners. For $245 you get the rest of baseball season and all of football season. No monthly fees. If you can learn how to navigate their site(I had to email them and ask this LOL) and find their daily picks you will win.
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I am using his managed account services. Only been using him for about 2 weeks, so no definite winning percentage established yet since i started. Around 60-65% so far I believe.
I have never heard of any type of bets like that before.
I know i have done If-win wagers where it is the complete opposite. You place a series of bets and once you lose, the rest of the wagers are not placed. Good money management way of doing it.
If you do it right, you play your strongest pick, and if you win and lose your next bet, you should still see a profit, but if you lose that first bet, that's it. the night is over and you don't have to worry about losing a second one.