Therefore I ask you: "What would you do if you were Greeg Leeds, president of WotC in the current situation?"
4e - The cycle of new edition, expansion, and eventual collapse has been pretty destructive to the D&D brand. Simply put, it is too expensive to keep revising the game over and over again. There is not a perfect game, and there never will be. With that in mind, I'd suggest looking at things third edition fans might miss about D&D, and see if there is a way to incorporate those things into future supplements, expansions, and options.
License Issues - With regard to 4e, I am not going to try to tell Hasbro how it's done. But very simply, the GSL needs to be revised to be less one-sided. As it is, WotC is playing the part of a noble benefactor, when in fact third party publishers have sunk a lot of time and money into development. Just as one suggestion, licensees should perhaps be able to continue using any version of the GSL that is less than two years old. It might not also be a bad idea to create a second license, one that has nothing to do with the D&D brand. The GSL is simply not set up to stir innovation; the usefulness of granting permission for people to create variant games is that there is then a permission to revoke if they start misusing trademarks, publishing obscenity, etc.
The OGL, although it represents the past in terms of WotC's business, is a vitally important link to a big segment of the D&D fan base. Not only should it be tolerated, but as publishers and hobbyists make requests, it might be worthwhile to open up more material. The rationale is very simple; stoke the heat. RPGs are a hobby for creative people, and keeping creative people creating, rather than angry and alienated, is going to help the industry. It does not make sense for WotC to try to continue to develop third edition alongside 4th edition; that would be a waste of resources. But if small publishers want to continue using the OGL to do so, a part of the fanbase will continue to be satisfied and will ultimately help build the D&D brand.
PDF policy - There is no ending piracy. And in fact, if you took all the money that will be spent in sueing eight people, and simply gave away that much in free PDFs to your fans, you would probably find it more profitable to your bottom line. PDFs have low inventory cost, so they should be an important part of keeping the brand evergreen. Fans who buy only a dozen hardcover books might eventually pick up any number of reasonably priced PDFs, simply because they are there and reasonably priced. Watermarking I view as the best way to fight piracy, because the consequences fall onto one person's reputation. Social disapproval is far more powerful than the law against a nimble adversary such as freeloaders. It is important to realize that the world is changing, and we do not know how this will be handled in the future. It is clear, however, that trying to treat piracy like shoplifting is doomed to failure, aside from the fact that many pirates have little or no ill will or greed. They are simply responding to what is available.
D&D Insider - Maybe I'm just not the target market, but I always find myself wondering, "Why do people want to pay a subscription for material many other companies would offer for free?" The focus should be on tools and lifestyle enhancements, not content. With content, you are competing, it must be remembered, with a considerable army of fans producing their own material absolutely for free. It should not be assumed that the typical D&D player is going to be a subscriber. Not going to happen. Ultimately, this has turned into a way overpriced fan club.