Doing two $50 price drops in a short timeframe looks stupid and may even look a bit desperate (even if it was planned), so I don't buy that. It's either a $50 drop or a $100 drop ONCE. Now as for when, there are two obvious possibilities:
1- Before Halo 3 (such as this rumour says): good press for MS, good sales for all games launched until then, especially if it's a $100 drop.
2- After Halo 3: makes more money for MS, which they'd welcome after setting the $1 billion dollars aside for repairs. However, this would piss off some Halo fans and give them less good press, especially if it happens that Halo doesn't boost the system's sales significantly; people would say MS is desperate.
Basically it's a choice between money and good press and customer reactions. Even though the 360 does need money, I think they need the latter even more, so I wouldn't discount those rumours as false. I just hope it's a $100 drop, not a $50 one...
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