The GDMC AI settlement generation challenge is a procedural content generation (PCG) competition about producing an algorithm that can create a settlement in the game Minecraft. In contrast to the majority of AI competitions, the GDMC entries are evaluated by human experts on several criteria such as adaptability, functionality, evocative narrative, and visual aesthetics - all of which represent challenges to state-of-the-art PCG systems. This paper contains a collection of written experiences with this competition, by participants, judges, organizers and advisors. We asked people to reflect both on the artifacts themselves, and on the competition in general. The aim of this paper is to offer a shareable and edited collection of experiences and qualitative feedback which have the potential to push forward PCG and computational creativity, but would be lost once the individual assessments are compressed to scalar ratings. We reflect upon organizational issues for AI competitions, and discuss the future of the GDMC competition.