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I am under the impression that if you own seveal sites you don't want to have them both link to each other on the same page. Like index.htm to index.htm. It seems ok to have them link to each others domain as long as it is not the same page. I found a lawyer that owns hundreds of sites each trying to get him different kinds of cases. I noticed that every page has his phone number on it. I searched for his phone number and came up with hundreds of sites all on the same IP and owned by him. They also all have PR4 or PR5. I called the number and some guy just answered no voice mail.
At the other end of the spectrum, Joe Blow Viagra affiliate probably adds little of value to the Web, and is much more likely to be booted if caught in a spam filter.