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"The time is ripe, you can bet he's prepared himself, as it won't be long now". Tobi was obviously talking about Itachi, whose time to live was about to end. Reason why Pain even reply by saying "so it's the time to get the Kyubi?"
I don't think that's referring to Itachi's sickness, but rather that the time is ripe for their battle (Itachi's and Sasuke's) and Itachi has prepared himself for it.