One: You want the worst house on the best block. Not the best house on the block, which is what this one is. Being king of the castle feels great, but there aren't a lot of kings bidding when it's time to sell.
Two: Buy a house that everyone wants. A home is personal, but it's also an investment, so when you're buying keep an eye on resale. Angelina's 11,000 sq. ft. house may have made sense for her and her gaggle of children, but she probably would have actually made money had she cut the square footage in half. There's a sort of functional obsolescence to the giant house…when you need staff to run a house (think Downtown Abbey), your house becomes your job. Not to mention the bills. Not many buyers want to take that on, particularly on the Eastside, which is why I think this GORGEOUS, very reasonably priced home is also not selling…
Three: Not everything goes up, even when it feels like it must. Almost 16 years into a bull run, entire swaths of the real estate industry (not to mention most of the Millennial generation) have never seen home prices dip significantly. It's easy to forget that appreciation isn't promised.