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Owners are usually oblivious to subtleties like PR and PR penalties, and often have only the most rudimentary understanding of how to calculate ROI on a paid ad or link. They hear numbers like, "We guarantee 100,000 views" and think, "Wow, that's fantastic!" without really comparing the cost of the ad, the click through rate, and the conversion rate to orders. You can help him through this quagmire...
I'm less sure about whether it might hurt you or not. I have been to many conferences where Google representatives have spoken and they have warned all of us to stay away from "bad neighborhoods". They have not fully explained what that means. One thing that is obvious is to not be hosted at an ISP what allows spamming and has been banned.
But, as for individual sites that are grayed out, no one knows what the Google algorighm is set to evaluate regarding links. But, they are evaluating for PR as a key part of their determining who might be a good site and who not, so I always err on the side of caution.
For whatever reason they are grayed out, I would certainly think through the association. One variable for your deliberations might be how many links there are in to your domain. If you have 50 links to you and a couple are questionable it would be different than if there were 2 and both were questionable.
Do they want to pay you to link to your site? If you can do that and you can teach me how to do that i will worship you forever!
Do they want you to link to them and pay you?
Do thay want you to pay them to link to your site? If they don't have google traffic i would want to know what traffic they do have that is worth paying for?
I might add, gstewart, that this is a good example of a "value added" service you provide by being a SEO-aware webmaster (and WebmasterWorld member!).
As for the real post...
>>>Will this damage my PR or my position in Google results?
Not if you don't link back to them, which you shouldn't have to do if you are paying.
There's so much link spamming going on (I get several link requests a day from some of the strangest places) that it's only a matter of time until google starts using link signatures to catch spammers and penalizes their sites.
Going after links from high PR sites on a grand scale is just another form of link farming and we all know what Google has in store for link farmers.
I'm sure all those PhD's at Google could, and probably already have, developed a link signature algorithm that can catch you link spamming in no time.
I say if you want to be a link spammer don't look like one. Look natural. Get links from relevant sites with a natural distribution of the web's Google PR's. Turn off your toolbar when you go surfing for link sources or exchange partners. Forget about Google and get links from sites that look likely to send you valuable link traffic. Even new sites with a grey toolbar may become good sources of link traffic in the near future. I wouldn't even be afraid of a blemished PR0 site if it's part of a natural distribution.
<troll> Heck, even Googleguy can crank up a link signature algo that will leave you with a massive headache if you link spam </troll>.
And we will always know what sites are appropriate for us to have linking to us. And we will know how to approach them without looking like a spammer because we aren't.
Hey, the bottom line is getting good, pre-qualified traffic, Google PR helping with that is a side benefit.