just ask to all the smart guys who tried this on expiration day in oktober 1987 what happens when you try to be too clever
You need to have $1,600,000.00 to cover the initial option margin requirement. Not to mention it is extremely risky. AZO 2009 February far OTM jumped 3000% on the expired day.
aside from the risk factor which everyone is jumping on, no one has mentioned that practically speaking this idea won't work. good luck selling 10000 deep otm contracts the day before expiration. which option has that much liquidity? only atm options have decent volume near expiration. this idea only works in a demo account.