Lots of good comments on the Stock Gamble update.
I agree that buying/selling stock in short term moves is not for most people. Frankly, it is not for me.
But, this is something that Mr. Sam is interested in doing, he is using a small amount of money, he is researching, tracking and has a plan. So I support the experiment, because I support Mr. Sam. I also recognize that Mr. Sam's plan is a gamble and I'm prepared for him to lose the full $5,000 allocated to him. But, I feel that it is a worthy gamble because I want Mr. Sam to be more engaged and involved in our personal finances.
I also agree that it is very difficult, especially for a small investor to "time" the market, but that doesn't mean that someone can't find and undervalued stock, buy it and set up a limit order for when it hits a certain value. If you do that enough times, rolling profits in from prior buys it is possible to make money.
I think the issue of when to sell a stock is interesting and one I've been researching and plan to post on soon.