Squatter's opinion is the same one that I gathered. The power of the elves must be more potent the closer to the Blessed Realm, and I guess Bombadil was hoping to intrust his little friends to greater powers once they left his lands. Or maybe the openings of the Barrows faced the east, like some huts of native americans faced the rising of the sun (only, of course, the Barrows didn't care hide nor hair of the sun, instead maybe looking towards the evil of Mordor) and he was hoping that they could sneak around...? THAT'S a stretch, though. I don't remember reading anything like THAT.
'Vana
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