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I also asked this question on Lang-8 and these are the (translated and paraphrased) answers I received. 当て here means the second and third definitions here. It is somewhat similar to 見込み or 見通し. One of the comments specifically wrote the following: 「当てをつける」=「見当をつける」=「見込みをつける」 見込み ≒ prospect, likelihood, possibility Therefore, the meaning would be "He ...


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I believe they are just saying that they could have allocated the funds to go on a trip if they wanted but they couldn't come to a decision. The third meaning from here: https://dictionary.goo.ne.jp/word/%E5%BD%93%E3%81%A6%E4%BB%98%E3%81%91%E3%82%8B/


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