Offer your thoughts or opinion on the input financial query or topic using your financial background.

What should I consider when I try to invest my money today for a larger immediate income stream that will secure my retirement?
I don't understand the OP's desire " I'd love to have a few hundred dollars coming in each month until I really get the hang of things. "  When growing your wealth so that it will be large enough in retirement to throw off enough profits to live on ... you must not touch the profits generated along the way.  You must reinvest them to earn even more profits.  The profits you earn need not show up as 'cash'.  Most investments also grow in re-sale value. This growth is called capital gains, and is just-as/more important than cash flows like interest income or dividends.    When evaluating investing choices, you think of your returns as a percent of your total savings at any time.  So expecting $100/month equals $1,200/year would require a $12,000 investment to earn 10%/yr. From the sounds of it the OP's principal is not near that amount, and an average 10% should not be expected by an investment with reasonable risk. I would conclude that 'There is no free lunch'.  You need to continually save and add to your principal.  You must invest to expect a reasonable return (less than 10%) and you must reinvest all profits (whether cash or capital gains). Or else start a business - which cannot be compared to passive investing.