I've never met anyone who liked taxes unless someone else was paying them, so you've got a lot of company. That said, the most reliable source of big time losses and major IRS headaches that I've seen in the last 40 years has been the tax-avoidance-driven investment.
My suggestion: Forget staying within the 15 percent tax bracket. Focus, instead on investing to keep your taxable income at or slightly below the level that would take you out of the 25 percent tax rate. This year that income level is $131,450 on a joint return after $20,000 of standard deductions and exemptions (including the elderly exemption), or $151,450. With inflation running at close to 5 percent, that's likely to be approaching $160,000 for 2009.
Remember, in a taxable account you have substantial control over when, and how, you take your income. You could put $2 million in the S&P 500 and collect only $40,000 in dividend income for the year and have virtually nothing in capital gain distributions. Even the addition of your $40,000 of real estate income would keep your taxable income below the top of the 15 percent tax rate, $65,100 this year. Once you turn 70 1/2, however, it will be virtually impossible to escape the 25 percent tax bracket.
Scott