I've bought 2 of my 3 lenses (an 18-105mm VR and the Nikon 70-300mm VR) 'used' (but in like-new condition), and saved quite a bit over buying them new. However, I bought them from a camera store, in person. I'd be a bit less comfortable buying a used lens from a 3rd party on Amazon, especially since they offer no real way for the vendor to show a picture of the actual product. I think in that case, even ebay offers more security. You can also see about finding a reputable forum member selling one.
I've never owned either of the 70-300mm Sigmas (the OS, or the 'Macro'), nor the 55-200mm Nikon VR, but I've been nothing but happy with my 70-300mm VR. It costs a little more than the 55-200mm (I paid just under $400 for mine), but has better build quality, equal or better optics on DX cameras, and better VR and focusing- especially the ability to override the AF without moving the switch to M, which drove me nuts when I had an 18-55mm VR. As well as internal focusing, so the front element doesn't rotate. It's not the 'fastest', either in aperture or autofocus, the lightest, or the best, but it offers an excellent compromise for the cost. It's also easy enough to hand-hold and carry, but so are the other three in this case.
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