We must remember that Gandalf, and many others of power can see the future. I think that it was all part of a larger plan. Yes, re-establishing Dale and Erebor gave the free peoples a mush stronger foothold it north rhovanion. I think that Gandalf aslo knew that Bilbo would find a ring possibly.
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"Understanding your people paves the road to understanding leadership"- Old Atreides maxim
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