i bet after the 10th option your account does not have enough equity to go short. "as many as possible" you are right. the buyer will be a professional unlike yourself.
for the record I once was an options broker (later became market maker) and I have seen some things in customers accounts were trades "just couldn't go wrong", only problem was it sometimes did and when it was the case their accounts got destroyed big time with debits way below zero. Pure horrorstories ! Never sell options saying 'this can't happen', cause it will one day ...
From what I am seeing, I think the bid price is .02 - is that correct? So you would only get $2 per contract, not $20. So, I'm not sure you would make very much if any real return on your money anyways. Anyways, if DNDN failed as a business for any reason before Jan 2010, you would stand to lose quite a bit. Also let me ask this, if selling 2.5s is "free money", then how about the 5s? How about the 7.5s? The 10s? and so on - what is the highest you can sell that is still free money? I feel there are better things I can do with my money then a trade like this in any event. JJacksET4