Also looking back to see forward I wonder just how quickly we will move through the product iterations. Will we see ~18 month cycles like AMD/Nvidia have shown in the graphics cards sector? What will we do with each lesser generation?
I'd say we'll never see that since I really doubt bitcoin mining will ever go 'mainstream' like graphics cards are. The sort of money we're talking about with manufacturing ASICs is peanuts compared to what AMD and NVidia spend on developing hardware. There just isn't the money in the market to warrant big expenditures.
Once everyone and their brother who is actually WANTING to mine bitcoins (and this is a FAR smaller amount than the market for other computer products) has an ASIC, the market will be saturated. The difficulty will go up and the only way to 'be profitable' will be to buy yet more and faster ASICs.
So it becomes an arms race and those with the biggest pockets will 'win'.
Therefore, it'll be like 'keeping up with the Joneses', like I said before.
I don't quite get your statement of "those with the biggest pockets will win"
What is your definition of winning? What is your definition of losing?
I don't really see how people with different levels of investment will be that far from each other in terms of ROI. A guy investing $1M in ASICs might see a 200% ROI, while a guy investing $150 in ASICs might see a 160% ROI. And the guy with $150 loses?
So, enough vague statements - tell me how the little guy will lose in this arms race.