The sentences work and it is common to use should have in this way. Although usually shortened to should've.
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Anonymoustwo questions1: Are the sentences correct with 'should have' in the sentences above? Yes, but you haven't got the meanings exactly right.
AnonymousJack usually goes to his office at 8am. Now it's 8:30 am; he would have gone to his office. Does 'would have' in your sentence work the same as in this sentence?That's not a good use of 'would have gone', so no, it's not the same as in my sentence. In your set-up, it's like this:
Anonymouscan I say,'he would be in his office now.', right?You could probably get away with that. Yes. I think I'd use "will", but "would" works pretty well.
AnonymousHow does 'would probably have finished' work in your sentence?I believe I already said that.
AnonymousDoes it mean it was the usual