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Generally, there's nothing wrong with different links with different text anchors as and when you can control them - but obviously there are advantages with trying to get links across more domains and IP ranges, rather than getting more links on a single page.
I do not know the right answer but let's build an example.
1. On page1 there are only link1 pointing to site1
I think that (almost) all page1 influence goes to site1
2. On page1 there are 2 links, link1 pointing to site1 and link2 pointing to site2. In that case the page1 influence should go to site1 and site2 divided in equal parts (almost half for each site)
3. On page1 there are 3 links, link1 and link2 pointing to site1 and link3 pointing to site2. In that case, in my opinion, almost 2/3 from page1 potential goes to site1 and almost 1/3 to site2.
Is it true? Does anybody know?
Although I do not have a direct experience with this scenario, I would never provide 2 links to the same URL (not site) from the same page; BUT I would surely provide 2 links with different anchor texts on the same page to 2 different URLs of another website.
I think it's much safer to proceed like this and may give you even better SE performance.
Best luck with your case and please keep us informed how it's going.
But, multiple links on the same page to a common page using different anchor text can work very well in my experience.
It's a great way to attract the attention of folks who might visit the page for different reasons, or who might get a better idea of what they'll find on the page.
I would't overdo it, but 2 - 3 links can work well for directing traffic.