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by CareyBot

In 2001, I was flush with cash, and I went home-shopping. I love the beach, and thought about buying a condo there, but my broker Gil said, "Buy a two-family home instead. That way, you can live in half of it and rent out half of it, and if you're ever broke, you can rent the whole thing out." Now I work for Gil, and I spent yesterday doing a direct-mail drop on New York's wealthiest ZIP code. Hand-address, stuff, lick envelope, lick stamp, repeat. Sometimes I daydream about how differently my life would turn out if I could just stop listening to Gil. But at that point, I didn't. I bought a two-family house, and rented half of it out, and lived in half of it for two years. Then I decided I couldn't hack being away from Manhattan -- for one thing, it was hard to have a good date while con...