One thing rarely taken into consideration, I think, when the subject of Drake's relatively limited commercial success is brought up, is that very few artists become greatly successful at all.
That's a very interesting point. It's often joked that only about 200 people bought the Velvet Underground's first album but that every one of them went on to form an important band. There's plenty of music (as well as books and art in general) that only comes to be appreciated after its time. In the case of some artists they're still alive and producing art when this happens so they get the benefit of it. In some cases, like Nick's, they're not around to see it happen.