I usually blitz read through this chapter, because I want to "get back" to Middle-earth. Tom's house always felt like a detour, but on this reading I'm noticing so much more.
1. The imagery of Tom holding the Ring up to his eye and the hobbits:
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Then suddenly he put it to his eye and laughed. For a second the hobbits had a vision, both comical and alarming, of his bright blue eye gleaming through the circle of gold.
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We have Tom holding the Ring up and his eye "gleaming" through the Ring, and perhaps the most widely known symbol associated to Sauron being the "Eye". I can't recall but up to this point in the books I don't believe "the Eye" has been established, or mentioned, as a symbol for Sauron.
When the Ringwraiths are near, Frodo gets a feeling he is being watched and wants to put on the Ring, but there's been no mention of Sauron's "Eye" yet.
2. All the hobbits dream in Tom's house except for Sam:
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As far as he could remember, Sam slept through the night in deep content, if logs are contented.
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I've always remembered this line because it's Tolkien's amusing spin on the phrase "slept like a log," meaning the person was knocked out all night, and when you "sleep like a log" you had a refreshing, very good night of rest. The other hobbits have disturbed rest, where they wake up from a specific dream, remember Tom's words and go back to sleep undisturbed for the remainder of the night.
This got me thinking about what does this reveal about Sam's character? He doesn't get pulled into Old Man Willow's dreams and he's the only hobbit in Tom's house who "sleeps like a log." Sam sees things for what they are, he sees through magic. If he was a character in the Wizard of Oz he would see the "man behind the curtain" and he pulls off masks.
He has some rather perceptive thoughts on his first encounter with Elves:
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"They seem a bit above my likes and dislikes, so to speak," answered Sam slowly. It don't seem to matter what I think about them. They are quite different from what I expected - so old and young, and so gay and sad, as it were."~A Shortcut to Mushrooms
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"Yes, sir. I don't know how to say it, but after last night I feel different. I seem to see ahead, in a kind of way. I know we are going to take a very long road, into darkness; but I know I can't turn back. It isn't to see Elves now, nor dragons, nor mountains, that I want - I don't rightly know what I want: but I have something to do before the end, and it lies ahead, not in the Shire. I must see it through, sir, if you understand me."
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Quite different from the Sam who just a few chapters ago was jumping up, squeeing about going to see Elves. Sam can't describe what his purpose for going with Frodo is yet, but he is the only hobbit who (up to this point) isn't fooled by magic, and sees people for what they are, not who they appear to be. I'm keeping this in mind when approaching the Strider chapters, because if I recall correctly, it takes a while for Sam to trust Strider.