The best type of examples I use for myself - when I'm looking at what the stumbles and trials of production can be - are the examples I see with indie producers/developers. I like watching these because they can often be extraordinarily public, since the indies don't have much in the way of compunction about being forthright with their issues.
It is with interest, then - at least in passing - that I've watched some of the trials of Notch in his rise to indie megastar. His most recent issue has been a bit of a hassle with the legal team from Bethesda Softworks in regards to his attempt to publish a game under the title "Scrolls." Bethesda is, of course, the developer of the highly popular "Elder Scrolls" series (although they are more commonly known by their episode title, e.g. "Oblivion" or "Morrowind").
What initially appeared to me to be an uneasy case of a larger publisher wielding a heavy hand has gradually morphed into a situation that I've allowed myself to learn is a bit more complex, and more importantly, it has been a valuable lesson on how taken in planning for generating IP can be critical in terms of reducing fallout.
An obvious, but necessary, caveat - as neither an involved party or a trademark lawyer, I certainly don't have the expertise to be fully accurate in my reflections here. What I initially saw here was this: Company "A" tries to publish game with similar-sounding title to game of Company "B," although those in-the-know would easily be able to distinguish between the two. I don't know that I was quite as initially reactionary as many, since I do understand the necessity of defending a trademark in order to keep it strong.
However, what I did intuit this as was a simple unfortunate situation that would eventually be resolved by the strong arm of a legal team. What I learned later, through various blog posts on the subject, was that the issue is a hairier one - Notch actually tried to trademark the "Scrolls" name. This would be fine, and eminently logical in most cases. However, it's not difficult to see how Bethesda is rightfully concerned in this case. Several pieces of commentary on the subject correctly pointed out that, at some undisclosed time in the future, if one company that was not Bethesda were to hold the trademark to "Scrolls" within the context of "fantasy video game" that spinoffs - like "Ancient Scrolls," or "Older Scrolls," or some other similar-sounding variant to "Elder Scrolls" - would be much harder to defend against, since the second trademark holder would be simply applying a modifier to their original trademark.
It was a point-of-view I hadn't considered, and I think that's it's a relatively well-thought-out one. What I can take from this is that ultimately, this may be a hard and embarrassing lesson for Notch to learn, and that moving forward as a producer, I can take away from this an understanding that (as in many areas) in IP development, an ounce of prevention can be worth a pound of cure.