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So when is it a good time to bring up the wife and kids when out dating?

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After years of a solid, unquestioned relationship

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Why, tho?

It is obviously weird in the first date, but I think it should be brought up pretty early in a relationship.

If they don’t have the same goals or view these things remotely the same way, why invest time in a relationship? Just to have it become a problem ahead?

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Yes

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