Am I afflicted with the obsessive whisperings (waswas) of repentance, or do I repent immediately after every sin, and is repeating this 50 times a day—due to matters such as delaying a response to my mother or believing I've been afflicted by the evil eye—considered a waswas, and what is the ruling on this action?

If the delay in responding to the mother is due to contemplation, then it is not considered a sin. However, if it is due to preoccupation with something other than an obligatory duty, then it is a form of disobedience (uquq) and necessitates repentance (tawbah). Repentance is legislated, but one must be wary of the delusion of believing oneself afflicted by the evil eye or disobedience without reason, as this is a debilitating illness. Repeated repentance, when its causes are present, is legally required, for Allah loves those who repent often, and the believer is "one who is tried, repents much, forgets, and when reminded, remembers."