The new taxes passed Dec 31, 2012 make a special dividend even less of a good idea.
Sure you can drain all the value from Dell, leverage it to infinity and pull $9 out, but to do that, the stock will go down $9 after the dividend is paid.
There is no magic value here. You have one large fund that is gonna get murdered on the loss here and they are willing to try ANYTHING to get out here.
If they go that route the stock will go up. Let's say it's $14 now and they offer a $9 SD. Don't you think that people will buy the stock to get the dividend. Of course they will, so the stock goes up. You then sell your calls.
But, yes you will not get the special dividend by owning the options unless you get it thur a price increase in the options or you execute your options prior to the SD, hold the stock on the day of issue or ex dividend date. And then get the actual SD. And yes you have the problem of the stock going down after the ex dividend day. So, hold the options and when the price goes up sell the options and get your return. Don't hold for the dividend as that would not be prudent unless the stock runs up to say $20 and they offer a SD on top of that price. Then, you may want to be in stock. I would not personally do that as the options at that point has probably doubled with a pps of $29. And then the price would drop by $9 after the SD.