It's not winning...it's just a very complicated suicide.
I don't know the man personally, but I believe he's as crazy as a fox at this point.
In the beginning of this latest meltdown, I agree with what you're saying. His hospitalization and stint in rehab were part of a tangential deathwish.
But I believe that Sheen had an epiphany of sorts during rehab, and realized that he had to act to salvage his career, and that this "madness" of his is all an act.
You know CBS wanted to can his ass for all of this; the last straw of a long line of personal foul-ups on Sheen's part. Sheen knew his termination was coming too while in rehab I'm sure.
Becoming off-the-charts-loco was, in my opinion, a business decision to get a new show that was 100% Carlos Estevez, all of the time. Whether, or not, it was his idea, the idea of his publicist, his agent, or perhaps even his father, I can't say with any certainty.
But just google "Charlie Sheen reality show" and look at the buzz.
Like this for instance:
Charlie Sheen Could Have Reality Show Deal With Mark Cuban
PS: The real genius will be if he can stay straight from here on out, and just play the madman...unlike Lindsay Lohan.