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My preference is to be right up front (or possibly to use "anonymouse" registration options to cut down the spam and junk postal mail.) One related backlink among many won't be a problem for Google. But if the entire backlink profile for a domain looks manipulated, then there can be a problem.
A reason why you should not be paranoid is also that google has become much smarter and it is hardly possible that anyone could push a site with some links from own sites. Such a linkgraph just will not work, it does not even need a penalty for that.
I'm normally more upfront too, but I'm thinking of trying something a little grey, and if it all goes wrong, I don't want my legit sites to suffer. So I think paranoia is the approach to take...I don't want any traceable connection between the two sites.
Anyway, you should not try grey things, it could stick to you for a long time.
[edited by: Robert_Charlton at 1:56 am (utc) on Mar. 7, 2008]