My view of things is that waiting for something is pointless. You want an upgrade or a new system asking whether to wait is also a pointless question, you do it now with what's out. Moreover, waiting is pointless since the next best this is always just over the horizon.
Sometimes waiting is pointless, sometimes waiting is useful.
Prices only go down if there is a pricewar, or if a new product has obsoleted the old one.
If you are a month away from the release of a next gen piece of hardware that has been on the market for 14 months already, then waiting 1 more month will give you a lot more for your money, since the moment the next gen hardware is released your current hardware is devalued.
Hardware is constantly upgraded, with old hardware sold and new hardware bought to replace it.
If X_0 is the price of generation N hardware at release, and X_1 is the price of generation N hardware when generation N+1 is released, and T is the time until generation N+1 is released, then the effective cost to you is (X_0 - X_1) / T
So if you a hypothetical chip was released on 1-1-09 for 200$ and is reduced in price to 100$ on 1-1-10 when the next gen chip arrives, then the monthly cost to you is (200$-100$)/12 month = 8.3$/month if you buy it on release day, and (200$-100$)/1 month = 100$/month
There is an additional cost for the sale of older hardware and purchase of new hardware, a a transition cost if you would. But that further advantages buying as early as possible in the product cycle.
Generally speaking we do not know when the next gen arrives. So it is hard to predict, but you can make general estimates.
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