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I hear the warning messages regarding the risks but I think with some care they are extremely manageable. In my case, I always keep a fair amount of cash around for various reasons so even a relatively expensive rollover or making a purchase in case of a large drop should not be a big problem (this is not even taking into account the transferring of capital from other investments). The one scenario where the risk can come home to roost is if Berkshire's stock price drops to around its -current- book value by 2016 making for an expensive rollover while the S&P continues its rise (as I have a partial hedge with S&P futures and options, a fall in the overall market should be fine) and most of my other ideas fail. Based on past history and reasonable considerations, the probability of this is low enough for me to be comfortable with. On the other hand, I put the probability that this does better than owning the shares with 2 or maybe 3 rollovers at over 80% (80% should be conservative), particularly if am sure to convert to shares if it ever reaches a reasonable estimate of IV.

I don't think that lack of LEAPs will ever be an issue given how capital markets have evolved in the past. Despite the high implausibility, I should nevertheless note that such an event will no doubt cause a major issue for this strategy.

There is no doubt that holding the calls is more speculative than holding Berkshire but I think, given the current Shiller P/E, that it might be less speculative than holding SPY provided one keeps to it for the next 4-6 years.
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