"Just when did I get to the point when staying at a hotel wasn't fun?"

Ira Glass is asking a rhetorical question about the point in his life when remaining at a hotel stopped being fun. He is assessing the modifications that have taken place in his life, and how his perspective has actually shifted over time. He is likely referring to the reality that when he was more youthful, staying at a hotel was a special treat, a chance to experience something brand-new and interesting. As he has aged, nevertheless, the novelty of remaining in a hotel has actually worn away, and it has actually become just another location to stay. He is wondering when this shift in point of view took place, and how it has actually changed his outlook on life. He is also most likely assessing the concept that life is constantly altering, and that we should adapt to these changes in order to stay happy and fulfilled.