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Don't cross-link between your sites - especially if you have many pages. I recently lost a popular PR8 site this way. It's a painfully effective way to flush six month's work down the drain.
If you have five websites, develop unique backlinks for each of them before interlinking.
Is that really what will keep you from getting a penalty? Make sure each interlinked website has backlinks from independent sources from outside you're network?
There have been many posts about interlinking, but no clear advice on how much interlinking is too much. Certainly I see interlinked sites show up in the SERPs all the time.
The thread that was linked to involved a guy who made 70 duplicate copies of one site and had all seventy sites having seventy links on each page pointing to the homepage of each of his 70 sites. That's a pretty extreme example. What happens with more moderate interlinking?
We had a set of 5 sites all doing great until they got a penalty.
Did any of the 5 sites have their own independent backlinks? Did every page of all 5 sites have links to the homepage of the other four sites? Did the sites contain any duplicate content?
And unless there is some obvious, non-SEO reason to link them extensively, I'd generally only have a few links back & forth. Certainly not a common crosslinking navigation element on all sites.
Natural links are the way to go unless you only care about short term results. If that's the case, go ahead & try the heavy crosslinking, it may very well work for a while.
If the sites are all unrelated, then there is no natural reason to link them, even if they weren't all owned by the same person and on the same IP. If they're too related, you've created a map.
They'll still need backlinks from outside sources - and if you get them all the same set of backlinks from those outside sources, even bigger flags.
But, it depends on your objective with the sites. If it is longevity, don't do it. If they are disposable domains, then you could give it a shot, just study up a bit more on A: the risks and B: sites you see doing it effectively that have been a long time.