On the topic of the Notes, I firmly am torn between the idea of the Helltaker doing a lot of random illegal shit to get his money, or him just having a normal day job to have a living.

Mainly cause the former makes sense, but the latter is funnier and probably would fit him well.

I doubt her viewer count is very high considering that she only plays turn based strategy games.
Maybe if she plays something mainstream like FE:TH.