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To me it seems like you're getting the worse deal, but I'm from the UK and think in pounds so +350 seems like a lot of cash difference. Go on ebay and compare selling prices of the two things (completed auctions, you should be able to find the same specs). Then see what the cash difference is. I personally would be inclined to haggle him down then also, ebay prices are a bit inflated.

Why are you doing this? The iMac is a great system.
 
Need someone from the US to chime in, but I think I would be aiming for a lower cash difference, perhaps $200 maybe start with an offer of $150, and remind him that you have applecare.
 
$150, no more than $250. Since you got apple care and he doesn't... The macbook pro aluminium laptops can be cheap. I got mine with 4gb RAM for just $1200 Australian Dollars (33% discount compared to Australia's apple display price) by sourcing it overseas and getting it through my cousins in university (and selling the ipod touch).

Couldn't have done the same with an imac.

$1200 AUD is roughly $1000 USD. Which is only a bit over twice the cash you're proposed to paying.
 
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