Eric's right, there's just not a lot to this chapter. The main entrance to Mordor is about as grim and insurmountable as one would expect; we've seen the trope so many times now in so many different fantasy tales that it's almost cliche at this point. The evil overlord blockades himself in his chosen land or kingdom; a blasted, desolate wasteland that serves to counterpoint the proud, warrior state of the main military protagonists (Gondor in LOTR), and the idyllic, tranquil homeland of the protagonists themselves (the Shire). Of course, it's all symbolism, because once you start to think about Mordor, the realism falls apart. What do these vast armies of orcs and men eat? I think there's a throw-away line in "Return of the King" about how Sauron has farmer-slaves tilling the soil for his armies in the inner depths of the land, but that really doesn't and cannot explain all the infrastructure the Dark Lord has in place here. It's all right, though, because symbolism.
I suppose I've been spoiled by more recent series I've read where the antagonists are flawed human beings, rather than evil godlike overlords. I feel like those kinds of villains teach me more about myself and what I might be capable of, in the extreme instance, that Sauron and his ilk. But they call this sort of book "high fantasy" for a reason; the protagonists are struggling against an idea, more than an actual individual.
Like Jacob highlighted, the chapter devotes a large portion of its text in bringing home to the reader just how much the hobbits are in over their heads. They had no idea what they were going to do when they reached Mordor; they didn't know anything about it at all. This seems like an egregious oversight on Gandalf and Elrond's part. Didn't they even consider the possibility that Frodo might get separated from Aragorn or Gandalf at some point? Didn't they sit the hobbits down and have lessons with them in Rivendell? Like, Geography 101; Political Science 101; crash courses on diplomacy and negotiation with southern cultures (Easterlings, Haradrim, Gondorians, and the like) with an emphasis on culture and military structure. Nope -- instead they allowed the hobbits to frolic around the valley looking at birds and butterflies while the big important folk planned the adventure. Sigh. At the same time, though, this circles back to what I was saying earlier about the hobbits struggling against an idea, not against actual realistic antagonists. It's not a flaw (no matter how annoying) that the hobbits are clueless about how to accomplish their quest. For one, the text itself points out, as Jacob observed, that both of them figured it was hopeless anyway, but just didn't want to dwell on it. And two, the more naive the hobbits are, the more triumphant it will be when they triumph over Sauron, the ultimate planner (heck, he's been planning this conquest for 3000 years and he still manages to screw it up).
Jacob also reminds us about the inherent melancholy of LOTR. Absolutely -- this is a major theme of the book and one that will be brought sharply into focus in "King" after being forgotten, largely, since the Fellowship left Lorien. That is, even if the heroes triumph, entropy will come into full effect; the hold the Elves have over the land will be broken (because the Three Rings, tied to the One, will stop working); and men will slowly forget about them thereby. No matter what happens, it's a net loss for the good guys.
I do have to disagree about the timeliness of the poem in this chapter, though. I'm a fan of Tolkien's poetry and have championed it in a number of chapters where it's been written off as "boring" by everyone else, but here I feel like it's completely out of place. Have Sam sing it in the next chapter, where they actually meet the oliphaunt and the tone is a little lighter. It just doesn't belong here. I don't buy it as a spur for Frodo to finally decide to follow Gollum to Kirith Ungol, either. Sadly, unless I'm misremembering, most of the best poems are already past us, and those from here on out are just tedium. Poetry watch -- stand by.
On to Ithilien. I remember really enjoying the next chapter as a boy -- I'm excited to see whether it holds up.
I kinda assumed that Sauron kept the orcs fed through pillage--that is, the waste land is actually the impetus, not just the crude symbol, for Mordor's conquests of Middle-Earth. That is, maybe this war is in fact a resource war.
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