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You may be right and your cases with ODP and Webmaster World are quite valid but I would still call for cautious here.
I remember a few months back (I am a "new user" but an "old lurker") when Google implemented new filters and many were penalized, someone here (or maybe it was on another forum) raised the suspicion that he was penalized due to heavy cross linking between sites, meaning, links from every page of one site all point to one page at another site.
How is Google to know who a site owner is and if they own the site that its linking to
This is easy, when they suspect they can check WhoIs.
I had a 600+ page with a link on every page back to my own personal site, it ran this way for over a year with no problems
Well, I may be wrong... or you may have been lucky:-)
I wouldn't do it anyway, if Google don't penalyze it now, he may be doing it in the future. I am aiming at long range success over short time gains. I try to avoid anything that even smells spam. And this strategy sure smells like spam to me.