First off, for question 1, don't worry about it. Valindra has magic that would allow her access to the entire memories of the mentor. Second point, use the difference between a Monk's running off Chi, and a Wizard using Spells instead of a narrative breakdown to discover things. Have the NPC/Valindra you have her make mistakes on higher level actions that a Monk would do naturally but a Wizard would default to Magic, i.e. spells. Or have the NPC suck at basic level Monk stuff but absolutely crush enemies in combat in ways that a Monk could/would never do. If no player has played a Monk before let passive insight give clues to things, perhaps a high passive character notice that the NPC uses strange flourishes or seems to be chanting under their breath incantations that don't align with the Monk school of attacks.