Cuando era aprendiz asistía un día (...)
The verb "asistir" should be in simple past tense: "asistió".
In this case, using imperfect past tense would be similar to saying: "One day, when he/she was an apprentice, he/she used to attend a conversation...", instead of: "One day, when he/she was an apprentice, he/she attended a conversation..."
Also, a comma is missing between the adverbial syntagma and the next syntagma. It should be written like this:
"Cuando era aprendiz, asistió un día..."
en la cual esa mantenía...
Here, you can't use "esa" because of two reasons.
First: "maestro" and "parroquiano" are in masculine gender, and "esa" is in feminine gender.
Second: if you're referencing el parroquiano, this part of the sentence should be like this:
"en la cual este último mantenía..."
And if you're referencing su maestro:
"en la cual el primero mantenía..."
Following the order in which both of them are mentioned.
Because they are mentioned together, writing "aquél", "ese" or "él" would be unspecific despite being in singular form.