Converting single family to duplex

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I live in an area in which it is relatively easy to convert a single family home to a duplex (most residential zones will allow with some caveats).  The question is whether this makes sense financially?  Has anyone else done this successfully and what are the main considerations?

Assuming that you have to buy a relatively beat-up house to make the numbers work, I'm thinking a house flip might be more profitable given the willingness of home buyers to "pay-up".  Any thoughts?

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I would also look into converting to a duplex in order to increase monthly cash flow, and what the math behind that would look like.