If Ben Stein purchased any of those houses within the last 8-10 years (give or take), his assets have depreciated. And this is particularly true in the trophy markets he apparently favors. So it probably wasn’t a good investment. That doesn’t matter if 1. he lives in/vacations in (i.e. uses) residential property and 2. he can afford to pay the carrying costs, whatever the lower asset value is. The amortized value includes personal comfort and satisfaction: Stein’s “art” or “psychological gift.”

Otherwise, he needs to rent them out. (Sounds like it, if he owns three houses on an Idaho lake.) If he does, he needs to manage them himself. Not a good idea to live too far away, because management companies will eat up profits. He doesn’t tell us if he rents them or not, and whether they carry their costs. This kind of appreciation of real-estate “art” is the asset that keeps on costing.

“He never for a moment imagined that real estate would be as illiquid as it has become, calling it “a real serious and aggravating issue.” But he has no doubt that it will revive. “I think now that everybody’s down on real estate, it’s the time to buy it.”

That’s my takeaway. Owning real estate is tough if you think that the value of your asset will only increase, and if your enjoyment and profit depend on it. Otherwise, it is desperation time. Stein sounds like a realtor: “Prices are Low! Time to Buy!” Or a desperate homeowner: “Please buy my house(s)!”