Bose SoundDock + 30 iTunes $299
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The Bose SoundDock, the high-end speaker system for any dockable iPod (Video and Nano included), is impossible to find discounted. Literally, retailers are not allowed to cut the price and exclude them from coupons. So that is why this is worth a look. Crutchfield has it for $299 but with 30 free iTunes downloads (a $30 value) via this rebate, free shipping and no sales tax to most states. It is the best option for the popular system I've seen so far.
Get this Boston Acoustics SoundWare XS Special Edition Home theater Speaker System for $299.99 plus free shipping at Crutchfield. This was the lowest price we found by $100! This system features five compact satellite speakers and a 100-Watt powered subwoofer. Customer reviews rate high for this system, with most giving the product 5 stars (out of 5). Plus, there is no sales tax (except VA).