thrive v. prosper v. flourish

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It would mean you think it would be better if he were Bill Gates but he's somebody else. Should implies obligation or necessity where would implies possibility.

If we are completely sure for our guess, do we still use would? How can we express the complete sureness for a guess?
 
How can we express the complete sureness for a guess?

We do use terms like sure bet, but there is always an element of risk with guesses, no matter how small.
 
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