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Rowling has said that the people in the portraits are not fully realized -- they are essentially shadows of the people they were in life. They can repeat "catchphrases" from their lives and give off the same attitude, but they are not like ghosts in the sense that they think/process information/et cetera. So I'm not sure how helpful Dumbledore's portrait will ultimately be.
However, I do think Dumbledore will help out in another sense (pensieve or otherwise).
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