George, awesome post. Another suggestive possibility, to borrow from your astute way of phrasing, may be for stock option holders to weigh exercising the vested portions of their options prior to January 1, 2012. Such date being the new date that the exclusion expires, as I understand is provided in the law the President signed today.
Who said Twitter DOESN'T keep a record of your tweets? What's been said is that Twitter doesn't let users access any archive of your tweets they may well have, and that they may well continue to mine. Your point makes me want to revisit the standard terms under which users license their original tweets to Twitter.
Yes, you have to build the shelf life of the company into this. One model I have seen a Seattle investor use is to assume a shelf life of 12-15 years at best. But if you can return invested capital every 2-4 years, you have a good run. And if someone offers to take you out, you can measure your opportunity cost against the offer, i.e. you can determine whether the buyout makes more sense than running the company through its natural life cycle.
Yes, you'd have a better chance of accurately estimating the risk, and you would be in a position (control) to do something about it, trim the sails, fire the management, retain the management, whatever. Staying involved day to day has costs for sure, but Carnegie and others in the 19th Century seemed to model a way where they spent a half day on weekdays at best managing many, many businesses. It probably has a lot to do with whether you can motivate and retain good management to work for you.