Buying a prepositioned URL thats good in Google, bad in Bing
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whispering... dude.. if I was you I would remove those URLs... somebody could grab it.
I think that links disappear when almost any site is purchased.
In some industries there are lots of bought, bartered and traded links that might be lost. Getting the seller to swear on a stack of Bibles might not be effective insurance. So I would be spending a lot of time checking them out and not pay a price based upon the full set of links being in place a year from now.
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heh, the las vegas and casinos are just my example, it has nothing to do with cities or gamblin'

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ha ha... you had me salivating!
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Don't forget that in some instances if ownership on whois changes as well as the content then the domain could lose some of its age based trust, and therefore rankings. Though I have no idea how common place that is, I've just heard it around so possibly worth checking out.
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Depending on the price and ROI, I would recommend he considers purchasing as long as the links are not associated to a particular character or business ownership where they would explicitly be removed once the domain is purchased.
He could then work to build authority links on top of what is already there and improve positioning.
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I'm endorsing EGOL's comments but I'm going to add that it's a really tough call. I think he's right that those links can dry up (especially over time). I also think that exact-match domains are losing some of their value, and Google may start pushing that harder. Clearly, though, they still have value.
I think a lot depends on the content similarity between the two sites and how much you can maintain new content that's relevant to the old links. If you can really support the old site's audience and selectively 301-redirect (on a per-page basis), you've got a better shot. If you just buy it for the domain name and then gut it and 301 everything to the home-page, you'll start losing that link-juice fast.
Of course, it also depends a LOT on the price-tag, IMO. Any domain change carries risk, though.