3 problems;
1> as stated in the FotR, Boromir I believe suggested this very thing, and was countered [By Gandalf? Aragorn?] that it would take way to long.
2> to even do that still puts you closer to Isengard than any other power.
3> Clearly Gandalf sensed on sime level that the party heading out from Lothlorien was crucial, as proved to be the case.
*The Vial of Galadriel was crucial in getting through the only possible pass into Mordor.
* merry and Pippin, were essential to rousing the ents at the right time.
* Aragorn and Eomer also needed to begin to forge thier alliance of mutual respect, etc...
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The dwindling Men of the West would often sit up late into the night exchanging lore & wisdom such as they still possessed that they should not fall back into the mean estate of those who never knew or indeed rebelled against the Light.
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