Day 13.1: Investments: When Spending Earns

One of my unofficial rules for this 30-day experiment was to come into the game without a cent. The only money I was allowed to spend on advertising or optimization was money that I'd already earned. Fortunately, I've been able to keep that rule with little discomfort, using only free program to help me out. But what if I decided to break that rule?

I've had many options over the past 13 days to spend money as an investment to do better than I have been. Looking back, I'm glad I stuck to my rule, because there are so many things out there that I wouldn't have any funds left at this point, and most would have been spent on products I would later find were total ripoffs! But I've also begun to develop a strategy for when I do get enough money to invest (probably in a week or so, at the rate I'm currently taking it). How should I go about it? How can I know for sure something is worth it? I put together a bit of a list to help figure it all out:

1. Can I get a refund? Is there a money-back guarantee, and can I be sure to return the product/service if it doesn't pay for itself in the specified length of time?
2. Is it credible? Who is using this, and what success have they had? Can I find any dissatisfied customers on the Internet?
3. Is there a free alternative? I've been surprised at all the times I've found completely free alternatives to services that were charging an annoying amount of money.
4. Is this something I'd really use? There are some tools that I've gotten that, in the end, didn't do a thing for me. They did everything they were guaranteed to do very well, but it wasn't something that helped me. This goes back the the notion that you shouldn't go into online business unless you have a defined strategy to begin with. Does this service fit my strategy perfectly?
5. Is it a one-time payment or a subscription? Depending on the price and service, either one might be better than another. But frankly I don't want the horrible surprise of finding $20 taken out of my bank account every month for something that only gives me $5 in return.

There's my list so far, and I'll try to work on it more as the week progresses. I do think I could make a lot more with the right investment, but I don't want to be spending my money willy-nilly. Please follow me on Twitter (@onlineincome) for updates and tips, or join me in my Free Internet Money endeavor!