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I'm a language learner, so please help me out with this: Is it better to say
¿Dónde estabas ayer a las dos en la tarde?
or
¿Dónde estuviste ayer a las dos en la tarde?
And if it is better to say estabas, what is the reasoning behind that? Or does it even matter?
The difference between estabas and estuviste is the difference between the tenses called pretérito imperfecto and pretérito indefinido, which are often known in English by the shortened forms "imperfect" and "preterite". Both the options are correct, even though they don't mean exactly the same.
The imperfect denotes an unfinished or ongoing action or state, so ¿Dónde estabas a las dos? means, more or less, "Where were you spending your time when the clock struck two o'clock?". The imperfect estabas implies no intent; it conveys the idea of something that was just taking place during a given lapse of time.
The preterite denotes a finished or punctual action or state, so ¿Dónde estuviste a las dos? suggests the idea of "Where had you gone so that you found yourself there at two o'clock?". The Spanish preterit estuviste suggests intent: that the person went somewhere so as to be there. This is not unlike the peculiar English idiom used to convey the idea of going away, being in a specific place and then coming back: "Where have you been?". This would certainly be translated with the preterite in Latin American Spanish (European Spanish speakers tend to prefer the compound tense pretérito perfecto).
The distinction is subtle and, for the most part, irrelevant, but I have the feeling that if I were seriously questioning someone, for example, I would rather use the imperfect, unless I knew they'd been somewhere specific at the time, in which case I'd use the preterite.
Doesn't really matter.
Preference for the preterite (estuviste) or the imperfect (estabas) for that type of question varies from region to region. Both are correct.
Although the regional variant of Spanish I am used to would use "estabas" 99% of the time in your example, it doesn't really matter with this verb, estar. Basically, if something is or was ongoing, then use the descriptive past (estabas); if it's more pinpointed, then use the time-delineated past (estuviste).
But let's change the verb and see what happens:
A. ¿A dónde ibas?
B. ¿A dónde fuiste?
In A, we set the scene, for some sort of interrupting action, for example, Where were you going [when you remembered you left the stove on]?
In B, the going has been completed. A possible context for this question could be: the person went somewhere, arrived, left again, and returned to the point of origin (home, place of work, restaurant where this person and the interlocutor are having dinner, etc. This question is equivalent to Where did you go?
So in situations like this, it does matter.
