Obama has admitted freely in his ghost-written book to being a coke head. Don't think that will fly too far, esp in NY. Anyway, the possibility exists in NY to run on both the Conservative and Republican tickets, so he should definitely go for both parties' noms.
Listen, I used to work with Larry at Bear, and he is friend. I will definitely be helping him in any way I can, but he is defintiely not a conservative. He became pro-life when he became a Catholic, but he is libertarian on a lot of other social issues. He was once an active Democrat, who was involved in several high-profile campaigns before he went to work for Reagan. What he is is the best Republican we are ever going to get out of NY. Back in the early 90's, when I spent a lot of time with him, I was positive that he was going to be the nation's first Jewish President, and that he would run as a centrist Democrat.
Obama may have used coke, but the usage didn't destroy his life. There is a saying in the recovery community that there is not faster elevator to a "bottom" than cocaine. Larry hit bottom at Bear and came out the other side a much better man. I honestly believe that's what happened, and that's how I would spin it if I were his campaign manager.