[Legate of Amon Lanc]

I believe something was already mentioned before - like that the Company had to pick a route that was not as expected, and High Pass was probably one of the top possibilities. Since there were Mordor-uruks in Moria, I believe Sauron would see to it that even the goblins of Goblin-Gate were aroused and if it was needed, even though Eagles (one very important power that, I believe, was not mentioned) and Beornings were watching that region, one well-planned assault could do the main job and cripple or even eliminate the company. After passing to the other side, there were Wargs who could make quick raids deep into enemy territory. Even though "no warg dared to enter" Beorning lands, again, if it was well planned and with the advantage of wargs' speed the company could be surprised and people taken captive.

I believe Radagast could have played more important part here than it seems on first sight. I was playing with the idea a few posts earlier , but when I think of it, it seems quite important. But now I don't think about how Radagast could have helped the Fellowship if he WAS there, but what would mean if he indeed was NOT at Rhosgobel (and if Rhosgobel was by the southern end of Mirkwood). If there was nothing to watch the Enemy's movements on the eastern shore, he could have prepared a smaller troop of Orcs or other troops from Dol Guldur and cross Anduin on boats in the lands between the Old Forest road and Lórien. And that would be too much of a risk for the Company.

Last but not least, I believe that it was not much pleasant idea to carry the Ring through the Gladden Fields, even though it would be on the western shore this time. Also who knows how the area was passable (seems that it was quite swampy).