I'm pretty much a newbie at this, so I'm going to freely admit my ignorance and save you experienced folks the trouble of pointing it out! 
I've been reading Natenberg's book and, if I understand correctly, any single option that appears to be undervalued relative to the expected volatility of the underlying can be played by purchasing that option, hedging delta neutral, and then periodically updating the hedge back to neutral at some set time interval.
On this basis, I'm wondering if the OTM SPX/SPY calls are attractively priced at this point. The SPX NOV 06 1400 calls were trading today at about 7.8% implied volatility, 34 days till expiration. According to ivolatility.com, historical 30-day volatility has been bouncing around between approximately 7.5 and 8%, with 52 week low of 6.96% on September 28. I also understand that we are heading into a historically more volatile period, so it seems that buying volatility at 7.8%, betting on a vol increase, might be reasonable.
My questions are:
- What's the best means of hedging the long SPX calls? Choices that I can see are the same strike SPX puts (long side), ITM SPX calls, emini SP futures and/or SPY shares from the short side. Since I'm new to this and would like to start with only a few contracts the first two options don't seem practical, as the ratio of long OTM calls to long puts or short ITM calls would be fairly high to get neutral- probably not feasible with only a few long contracts.
- What's the optimal hedging time interval? Seems like the simplest approach would be to rebalance at the end of each day, thereby matching the ivolatility.com calculation method.
- Would a movement based re-hedging interval make more sense - maybe every time SPX moves 10 points?
- Will the trading costs associated with the frequent rebalancing eat up most of the potential profit? I'm on TOS and pay minimum $5 for stock trades, $3.50 per side for futures, flat $1.50 for options. Good time to open an IB account?
- Is this approach considered "gamma scalping", or is there another name for it?
- I'm concerned about the market getting quiet during expiration week when most of the theta he gets sucked out - should I scale out of the position towards the end, trying to keep position theta approximately constant? I think I remember reading that the market is typically more volatile during expiration week, so maybe this is exactly the wrong thing to do.
Thx,
-Steve

I've been reading Natenberg's book and, if I understand correctly, any single option that appears to be undervalued relative to the expected volatility of the underlying can be played by purchasing that option, hedging delta neutral, and then periodically updating the hedge back to neutral at some set time interval.
On this basis, I'm wondering if the OTM SPX/SPY calls are attractively priced at this point. The SPX NOV 06 1400 calls were trading today at about 7.8% implied volatility, 34 days till expiration. According to ivolatility.com, historical 30-day volatility has been bouncing around between approximately 7.5 and 8%, with 52 week low of 6.96% on September 28. I also understand that we are heading into a historically more volatile period, so it seems that buying volatility at 7.8%, betting on a vol increase, might be reasonable.
My questions are:
- What's the best means of hedging the long SPX calls? Choices that I can see are the same strike SPX puts (long side), ITM SPX calls, emini SP futures and/or SPY shares from the short side. Since I'm new to this and would like to start with only a few contracts the first two options don't seem practical, as the ratio of long OTM calls to long puts or short ITM calls would be fairly high to get neutral- probably not feasible with only a few long contracts.
- What's the optimal hedging time interval? Seems like the simplest approach would be to rebalance at the end of each day, thereby matching the ivolatility.com calculation method.
- Would a movement based re-hedging interval make more sense - maybe every time SPX moves 10 points?
- Will the trading costs associated with the frequent rebalancing eat up most of the potential profit? I'm on TOS and pay minimum $5 for stock trades, $3.50 per side for futures, flat $1.50 for options. Good time to open an IB account?
- Is this approach considered "gamma scalping", or is there another name for it?
- I'm concerned about the market getting quiet during expiration week when most of the theta he gets sucked out - should I scale out of the position towards the end, trying to keep position theta approximately constant? I think I remember reading that the market is typically more volatile during expiration week, so maybe this is exactly the wrong thing to do.
Thx,
-Steve