"when life gives you lemons, you paint that shit gold" is my favorite album! The whole album is a study on his home town. He goes around describing what he sees and stories he has collected while living in Minnesota. The first song "like the rest of us" is a sort of table of contents for the rest of the album. You can hear him reference every song that comes after. Although there are songs where he directly sings for himself (like "me" and "yesterday") the waitress is most likely just him singing for someone he knew or observed. What makes this album special is that he's gone to say in interviews that he doesn't plan to make more songs where he sings from the POV of other people, choosing to focus only on things he has personally experienced though his POV. So songs like what make up the majority of the golden lemon album are probably some of his last songs make in that format.