What I didn't expect the most was Wizard's insistance on the precise formatting of, e.g., references (in the SRD). Allowing you to use their template formats is great. Deciding, for you, that page references are a no-no is condensending. Insisting you use small-caps for the initial cite an italics for the following ones is... just strangely obsessive.
I am surprised that "will survive termination" is even possible. Can future changes to the license then be invoked? For example, if the license is later changed to disallow any backwards conversion into Creative Commons License as well as the OGL, would it be applicable to someone who terminated his contract before the change was enacted? I'm guessing no, but the whole idea of a contract binding after it's been terminated is rather new to me...
I was also surprised at the amount you need to kiss-up to WotC if you're gonna use this license. "Licensee will not attack the title of Wizards in and to any Wizards Intellectual Property" (so if Wizards claims to own the copyright to "Blue Moon", I'm supposed to not challenge that?!), "Licensee will assist Wizards to the extent necessary or as requested by Wizards to protect any of Wizards’ rights in and to Wizards Intellectual Property." (so now I'm your lackey? Now I gotta admonish people using your Yu-Gi-Ho names illegally in my country on your behalf?), "Licensee will defend and indemnify Wizards and its affiliates, and their respective employees, directors and representatives, against any claim ... brought by a third party,... any material contained therein that is alleged to be scandalous..." (so now I need to pay for your PR if my bokk caused someone to make some Chick-Tract about diabolism in D&D?)....
I am disappointed that the poison pill applied to content, not just product lines. This means that you can't have dual-statted works, no 3e and 4e stats for the same world (not even by partners - "and ensure that third party affiliates of Licensee cease their publication, distribution and sale"). Yet you MAY, if you reach an agreement with White Wolf, publish 4e and Storyteller mechanics for your content - madness! This is just designed to kill off 3e support, and of course takes True20 and so on down with it.
Otherwise, the contract is pretty much what I expected.
As a non-publisher, I would of course never use the GSL - unlike the OGL, which felt much more accomodating and simple. This is clearly much more a "this license is for buisness" thing.