Can you link from 200 pages of site A to new site B? yes
Will google know what you are doing? yes
Will google devalue your sites? maybe
An expert will never do it this way. They will link between there sites using personal name on one site then business name on the other (or something similar). Thy will generally not leave any sort of clues that the sites are owned by the same person.
Then there are those that use private registration or use a whois guard. From what I've heard google can see through this as well but when you think of it there are tons of people that use autoblogs to link to their main sites.
So the idea is to decide for yourself where you should draw the line. I personally am more on the white hat side and would not do it this way. I have tons of feeder sites but they come from web 2.0 properties or something along those lines.
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