I have ~160 domains on one IP and quite a lot of them link to each other and they range from Google PR3-PR6 (and a new one at PR0) so I don't think it does them any hard from what I see.
Linking between "Like Minded" sites is always good. Linking between sites just to get your link count up however is not an advantage. For example linking from a Book store site to a site discussing Authors is definitely "Like Minded" and would likely bring some advantage. Linking from an Archery site to a Builders Merchants site is not on the face of it a relevant link and would be of no advantage.
Now we come to the same IP bit of the question. Linking between sites on the same IP is not detrimental in itself, but what it will do is make any "Contrived Irrelevant Links more obvious. That is the one and only downside to the shared IP issue.
Remember also that too many reciprocal links can also set a pattern that appears to be contrived.
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