While more frequent dividend payments mean smoother income streams, investors should choose their monthly dividend stocks only after conducting robust due diligence on a company’s core fundamentals, and not solely because of its high monthly payout history. By Marc Pearlman. That’s why income investing was such an important discipline that every trust officer, a bank employee, and stockbroker needed to understand. A better choice may be bond funds, which you can learn all about in bonds vs. All else being equal, an income investing portfolio structured this way wouldn’t run out of money, whether you lived to 67 or years old.