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What made this the worst thing? ....as compared to losing the Shire, for example? Or do you see that as tied up in the Ring?
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Frodo succumbing to the Ring (sooner than he did) would have meant utter failure for everyone. The Shire would have been lost anyway. It would have been turned into a strip mine if Frodo had failed or done nothing. The Shire was gone for Frodo.
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Do we ever face that kind of thing? ... at least by analogy?
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Yes.
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However, I think Frodo's biggest problem he faces is actually taking the Ring, which takes great courage.
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I'm afraid I must disagree with this. Gandalf says (when he is talking about Pippin joining the Fellowship) that Frodo did not really know what he was getting himself into. While it was undoubtedly an act of courage, it was not done with foreknowledge.
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Frodo had to battle with losing hope.
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I'm not clear that by the end (particularly after his Cirith Ungol experience) Frodo had hope. I think it was more of an act of will on his part to continue the journey and resist the Ring without hope.