He gets absolutely livid when people treat him like everyone else. He flat out said in his AGT suit that Marathon violated the ADA because they treated him like everyone else. He believes that the ADA mandates special treatment. He tunes out anyone telling him anything he doesn't want to hear, so even if someone did try to explain why he's wrong, it wouldn't register with him.
And yes, he has absolutely no idea how famous people, even minor celebrities, live. He thought Farrah Abraham ran her own Facebook account. He didn't understand that Taylor Swift's agents did exactly what they were supposed to do in rejecting his song. He also doesn't understand delegation. When he sued her the first time, at most the only thing that happened was the head of her legal team said "some weirdo in Utah is suing you for frivolous reasons. We've retained a local attorney to deal with it." She pays people to worry about the little shit so she can concentrate on being Taylor Swift and all that entails.