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He will have had the operation by may and should be a lot fitter then.

Have I phrased the sentence correctly? By this sentence, what I understand is -He probably will do the operation- in future- by the time which is mentioned.

In addition, what does the following mean?

....should be a lot fitter then.

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Yes, the sentence sound fine to me.

....should be a lot fitter then.

It means he should (you are expecting him to) be more fit than he is now.

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