Quote from toswilliam:
Thanks for all the input. I am still testing the strategy and this month with the exception of the 31 where I was in and out of the trade 13 times x $7 comm on each full trade and a few missed ticks brought me to -$150.00 on the day. It has blown right past the naked short position and has maintained a very close hedge. I realize this could eat up alot of premium if it stays in the channel but in this case I will probably be 4 or 5 days without and risk on coming out of the futures contract. My thoughts are now that it would probably make more sense to sell the put and the call just out of the money to collect more premium on the front end so if I get caught in a few more days like the 31st it doesn't eat through the premiums collected.
There is more variation on the emini to the spy than I would like. I am also going to test on the futures options so price would directly coorelate and be a perfect hedge. Less slippage.
It is alot of work and possibly alot of commisions but I am looking to hedge as close to 100% of my trade as possible and just collect the time decay. At current volitility selling the call and put just out of the money you would collect 2.50 on each side. $2,500 in premium even if I spend $1000.00 protecting the position after taxes I am still making 5% on the trade.
I think your on the right track using ES Options to hedge SPY options risk. From very limited data it appears at any instant in time ES and SPY are not 100% in sync. 1 ES strike to 4 strike differential.
The shot gun approach seems to work well. Scalp sets of ITM and OTM option pairs and as quickly as you can offset open new positions. These positions appear to turn every 3 - 10 days.
Biggest issue is dealing with your broker. Even though you appear to have a near 100% hedge they will not recognize the cross instrument hedge.
As far as they are concerned you are naked shorting SPY and buying ES options for cash. You will receive a premium and cash gain but all proceeds will remain encumbered until you unwind the trade.
This is a shame because the trade pair itself provides sufficient SPY premiums to pay for the ES Hedge and profits to boot.
I suspect unwinding and settling the trade is not an entirely clean transaction.
Looking at expiration data and the following trading session there is an awful lot of play and back room steam rolling going on.
Overall, you've got a Good Arb Idea, Develop it and propser... good luck