Well, if the 8GB iPhone drops to $299, then the 8GB iPod touch would have to drop to $199 or $249, which might make it hard not to drop the iPod Classic prices too.
I think either we'll see a price drop when the 16GB iPhone is released and a 32GB iPod Touch will accompany it to replace the 16GB and the 16GB will replace the 8GB, or the iPhone prices will stay the same and they'll release an 8GB 3G second generation iPhone at the current price point or $100 higher.