Quote from TskTsk:
Thanks newwurldmn, this answers a lot of my questions.
However, regarding #5, say I want to replicate a variance swap. What I'll do is basically short straddles all over the place, at equidistant moneyness, say $5 or so between each straddle. Now here's the thing. The straddle I short ATM is going to earn me an extrinsic value of for example $5 in total. But the straddles I short ITM/OTM, are going to earn me extrinsic values of less than $5, and it gets lesser and lesser the more in/out of the money the short straddle is. And if price now moves to one of my deep short straddles, and it becomes ATM, it's extrinsic value is going to increase beyond the initial extrinsic value I shorted it at. Won't this give me a disadvantage? Theta will obviously also increase as it comes closer to ATM, but as far as I see, that theta increase won't benefit me in any way, because I don't have enough extrinsic value to realize the theta. People who shorted it while it was ATM on the other hand, have enough extrinsic value to realize the theta.
Or am I overthinking it?
First of all, no need in trading straddles. Just trade the out of the money option (puts on the downside, calls on the upside).
Secondly you are right. If the spot moves fast, you will lose money. But at this point you need to look at the portfolio as a soup of risk instead of each individual option.
Suppose the stock moves slowly down (so you are able to stay constantly delta flat). What will happen is that your atm options will be decaying a lot and they will also be becoming out of the money options. At the same time your out of the money options are becoming atm options. You can view these as offsetting.
If the underlying moves quickly down then you will have delta/gamma issues like you would in a single strike short straddle scenario.
FYI - This is very tough to implement in real life. It's hard for even banks to synthetically create variance swaps.