I'm also using an '08 imac running 10.9.1 and it runs fine. The OS is not impededby the age of the hardware at all. That being said, it does take some time for some tasksto open. I see plenty of beachballs but it's not much of a hindrance. I've maxed the ram and try to keep the HD lean but find it difficult with four users installed. I find myself asking the same question though. I'd love to have the new imac and was just before this costing out a BTO 21" and figuring whether I can afford the payments. (I can't, yet.)
So, really, you can go either way.
But if you can afford it, brand new IS best.
Hope this helps.