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One that came up recently - should I buy rental property to guard against a stock market crash? We know if the markets correct that dramatically, people would theoretically move to bonds, so the value of the bonds would go up. With the real estate market just as hot as the stock market, she would buy that rental home at the same time everyone else was trying to get into real estate. Truism #1: Investing in direct real estate may be appropriate in two situations. Truism #2: Be careful about going into a real estate investment with friends or family. Truism #5: Counting on a large portfolio of real estate to sustain your retirement plan is not very smart. People who counted on real estate income in 2009 ended up very stressed and losing their shirt, especially if they leveraged their properties. I have this gory real estate discussion with clients too often and decided as long as a real estate investment isn’t going to torpedo a financial plan, I don’t fight it much. They fear the markets when the market is in the doldrums and love the market when everyone is making money. Real estate is no different.