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Well, since he was so sure that nothing could stop him (and one must admit his arrogance is well founded) he didn't want to send any small raiding groups, but to finish off all of his enemies situated in the east in one move - Dale, Lorien and Gondor. The others would then have fallen sooner or later.
The only mistake in his plan I see is letting the ways into Mordor so unguarded, and especially leaving Orodruin unguarderd; a small group of Orcs at the entrance would have been enough.
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“The invisible and the non-existent look very much alike.”
Delos B. McKown
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