1. I think he handled the obstructions well. Aside from the second one, he met the requirements asked for by Trier.
2. I find obstructions helpful because they give you some general guidelines to abide by but they generally aren't that restricting. As a result, it is still possible to have very diverse projects even though the obstructions were the same. I tend to like obstructions because they give you a start on what to do and then the rest is up to the artist.
3. The film served as a good reminder on why there are obstructions set and how they can actually help/