Dilemma - which to keep?

I currently own 2 Macs, but due to starting a full time job I can't really justify having both any more. I have:
2006 Mac Pro, 2x2.66ghz Xeon
2009 iMac 27", 2.8ghz i7
I'm having real trouble deciding what to keep. Both are probably worth roughly the same. The iMac is a great looking computer, is fairly new, and does everything I need it to NOW. But it has zero upgradability, apart from RAM. The Mac Pro is quite old now, but is still very expandable.
The iMac obviously has the newer i7 processor, but is it going to be any faster than the dual Xeon, which is also quad core? Is the 2006 Mac Pro any different to current models in terms of upgradability? It looks identical to the current one. Are processor upgrades easy/possible in future?
Basically as both are worth about the same, I want to keep whichever I can keep up to date for the longest, and more importantly, alive the longest. I'd appreciate any advice.

You answered your own question with this sentence: "I'm not a hardcore gamer or anything, in fact I'm a web developer which requires very little power." This means you're better off with the newer Mac and don't have to worry about upgrading. The only thing you might want to upgrade is RAM (that iMac can take up to 16gb, which is twice more than plenty) and nonvolatile storage (that iMac has FireWire-800 for fast and easy external storage). The iMac will also run quieter and pull less power.
But the Mac Pro is a fine computer, and a lot depends on what kind of monitor you use with it, plus any extra cards or multiple internal drives you might have installed. Of course, the monitor you're using with the Mac Pro can probably be set up as a second monitor for the iMac.
For me, this would be a no-brainer: Given your stated needs, the iMac is the way to go. But so much depends on personal preference, you're going to have to go with your "gut" in the end.

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