I haven't achieved anything by buying options, except maybe to identify two reasons why I don't like to:
1. The limited lifetime puts me in a very disadvantaged negotiating position. The pressure to sell for even a relatively small profit is hard to ignore, since the buyers need only wait for expiration. And then the big commissions and the big spreads. All this leads me farther and farther into the money. But so then why bother?
2. The damn things are so flaky that I don't feel I can put much money in each one. And they take a lot of watching. And I tend to get worried and watch the ticker all day. Lots of time spent for relatively little money invested.
I don't know enough to comment on the mechanics of option exercise or the risk that somebody doesn't/can't pay. Buffett recently expressed the opinion that derivative securities in general are no sounder than the entities that back them. So naive or disingenuous "risk management" programs based on these things can fail, backfire, or just cost way too much.