Thank you for the kind words.
I started writting this after watching Kokoro Connect. I really liked the idea of being unable to tell if the entity is a trickster-mentor actually helping to strengthen their friendship and budding relationships or a jerk whose victims get closer to each other the same way soldiers in a warzone do.
So yes, I do plan to make sure Leonard and Jon consider themselves 'Blessed with Suck' and thus keep them at least slightly miserable at all times. Overcoming challenges is what most fiction is all about, after all. And now that I'm done with Jon I'll return to Leonard and his challenge of wearing a skirt, succeeding and cursing when the Entity thinks of new ways to keep things entertaining.
And if you are reading this chompy: Thank you for the warning about quickly escalating powerscales ruining stories. I double-checked my plans for Jon after that.
In Jons case "The path of a Magus is to walk with Identity-Death" would have been a more fitting warning. That should be enough motivation to keep him modest.