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The title is a variation of the following example.

Should there be a question-mark before semicolon? the part after semicolon is also part of the dwelling. should the punctuation be different?

He dwelled on what if the path had been different; could he have taken it?

Based on a comment below, is this correct?

I dwelled on "what if the path had been different? Could I have taken it?"

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    Me, I'd use a colon. (But I'm old-fashioned and would use 'dwelt', too, following Wordsworth.) – StoneyB Dec 14 '14 at 19:56
  • '...what if the path had been different' is a rhetorical question in this case, as is, '...why that happened' and needs no question mark. – Joe Dark Dec 14 '14 at 21:10
  • Does the question mark then apply to "could he have taken it?". There are two different rhetorical questions in the sentence and I am not sure if the sentence punctuation is capturing it fully with the semiconlon and question-mark. – Joe Black Dec 14 '14 at 21:58
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    'He dwelled on what if the path had been different' is an anacoluthon. Using a quote structure "He dwelled on [the thought] 'What if the path had been different?' ... Could he have taken it?" works. – Edwin Ashworth Dec 14 '14 at 22:03
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He dwelt on what could have happened had the path been different. Could/Would/Might he have taken it [then]?

This uses the subjunctive to express the counter-factual condition you wanted without using an explicitly stated thought. Choose "could" to focus on whether it would have been possible, choose "would" to focus on whether it would have been that way, and choose "might" to focus on whether it might have been different. But there is still substantial overlap between the three, so more than one of them may be appropriate.

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