I agree. When I finished the article, I thought: File this one under "Problems I'd love to have." I can't imagine agonizing over any of the examples in the article, and I don't see the difference. I have a tiny handful of friends with gobs of money and that doesn't make hanging out with them awkward, regardless of who pays. Honestly, if one of them were to rent a house in some exotic location and invited me, I'd be thrilled! The article feels like it is from some alternate universe.