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should is used to give advice. In this case, you're giving yourself an advice an not an obligation. Debo is for a personal obligation. So, we have ¿Qué debería comer para mantenerme sano? ¿Qué debería comer para quedarme sano? (Literal translation of the verb stay.) ¿Qué debería comer para estar sano? (Most common way to say this.) Note that ...


I don't follow your two different rationales, but in any case the correct translation is: Qué debo comer para mantenerme sano? Additional mistakes: 'To' here means 'in order to', which is translated as 'para'. 'To' in the sense of 'towards' would be translated as 'a'. Mantenerme the reflexive is in the first person.

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