B: Henry has always been a money-minded person. I wonder who he would marry.
First of all, are the sentences correct above? If yes, how do woulds work in the sentences? Are they conditional woulds?
(A) is OK. "would" is past tense of "will" (they wondered "I wonder when he will settle down"). (B) is possible if you are talking about his willingness.
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(A) is OK. "would" is past tense of "will" (they wondered "I wonder when he will settle down").
(B) is possible if you are talking about his willingness. My guess, though, is that you probably don't mean this, in which case "would" should be "will".