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No it won't be endless because all we are trying to do is not buy on the wrong side of a product upgrade.
Much of the rest of what you say is unsubstantiated assertions of what will prove in the end to be wrong. To backdate your assertions, "iMacs won't ever ship with upgradeable Video cards nor 2nd monitor support, that's what Mac Pro's are for" and Time Machine will have a hard time backing up reliably to a drive that is not necessarily connected or turned on.
iLife does ship with new iMacs and the existing versions have flaws one can only hope will be fixed in the next upgrade. I never said iWork gets sold with new Macs, but my son would be buying it with his proposed iMac and simply doesn't want to then in short order have to pay all over again for the next version.
The computer my son is aiming to buy is the shipping iMac 24" with video card upgrade. But that computer will be cheaper and/or better speced in the due upgrade.
To repeat myself, he is trying to avoid the extremely expensive upgrade to Leopard, iLife and iWorks because he will want those, and knowing Apple it will also freeze out certain features from slightly older Macs. Best not to have those just before a major change.
Seems quite obvious to me, I don't know why you are struggling with this, unless when you shop with Apple you just open your wallet and ask Apple to help itself, because it is all going in a good cause. ie Steve Jobs' backdated options.
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