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I'm a subscriber to the Fool Advisor newsletter, not the HG newsletter, but if HG works like FA, where you get two new recommendations each month, then here's what I'd recommend you do:

Each time a new newsletter comes out, pick one of the two recommended stocks and buy $1000 worth of that stock. This will gradually move your money into the market and will help make sure that you buy stocks close to the price at which the stock was recommended. Also, by purchasing $1000 at a time, you keep commissions to 1% (assuming a $10 commission). Once you exhaust your extra cash, save up cash until you reach $1000 before making a new purchase.

You might consider a simple discount broker like Scottrade, which only charges $7/trade and puts no restrictions on how you trade. I've been very happy with them. I think ShareBuilder limits when you can buy and is set up more for someone who wants to regularly buy small quantities of a particular stock.
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