I've read all five pages of this thread, and ShadowWind comes the closest to nailing it. There's nothing "illegal" about what Jim Hill was doing. The problem is that people here are confusing legalities with rights. DLR, being a private property, has the right to ask anyone to leave the property for any reason they see fit. Period. It's no different than your home turf or mine. Whether or not it's "smart" for them to exercise their option in this case is another question. The flip side of the coin is that Hill has no "right" to run the tour on DLR's property. "Free speech" doesn't matter on private property. Hill can say what he wants about Disney, but he can be made to say it off-site.
As for the international tour guide analogy, there are several key differences. Even though the guides may offer info about DLR as they walk their charges from attraction to attraction, their primary function isn't to dispense knowledge about DLR... it's to help the tourists experience the attractions. If Disney were to start doing this, my guess is the folks with the pennants would start to get grief from Disney too.
Other key differences that I read and spotted:
1) Hill started his tour in the same general area as the official tours.
2) Per the photos (*) it appears that Jim Hill did the tours wearing a GOH badge. I know from wearing those that a LOT of people mistake you for a CM.
3) Disney also offers a tour that's about the history of DLR.
Given the above three points, it easy to see the confusion that many guests (particularly inexperienced ones) would have in differentiating between Hill's tour and DLR's. You and I know the difference between the GOH and CM badges, but to a first time visitor that often isn't so. In the world of marketing, you don't want other people confusing your product with some one else's... and DLR, particularly due to the complaint filed by the three ladies, decided that enough confusion existed to try and do something about it. True, the ladies may have been numbskulls, but that doesn't make the situation any less of the headache for Disney with they complained about it.
As for his CD idea, I think it'll fly and Disney can't touch him on the matter. He can position it as a audio "publication" and as such be allowed to use Disney's trademarks under the "editorial" section of "fair use" law.
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