It's definitely risky if you cross-link among sites that you own--even riskier if they're on the same IP or on the same class C block.
My take on it all is this, though:
Essentially, you don't want your little network of sites to be located on an island. You want your sites to be a good member of the Internet community--which means that you need on-topic links in to your sites from other websites, as well as on-topic links out to other websites. The better member of the Internet community you are the less you will have a problem with your own little network of websites.
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