It's a mathematician's answer. :P

Bejeweled 3 has Zen Mode, which can supposedly help you to relax and fall asleep. But generally speaking, games are probably not something you should be playing before bedtime as it is a mostly stimulating activity. Try reading, deep-breathing, light yoga, natural supplements, and laying off caffeine/alcohol/nicotine before bed first, and if that doesn't work, it may be time to visit your doctor.

Never played, but I don't think a game as highly polarizing as Dark Souls should be considered in the running for a universal game of the generation. A title like that should be reserved for a near unanimously acclaimed game that helped push gaming to a new level in some way, whether it was from innovation or exceptional refinement of traditional mechanics.

Mother 3 and Spec Ops: The Line put a lot of video game stories to shame.

This is true, although you have to wonder if one day some of us will end up doing the same exact thing our parents did, i.e. forcing our kids away from some new unknown entertainment medium that we have no idea what it could do to them.

Too pricey, not enough games I want, and I have too much to play at the moment. I also want to invest in a gaming PC soon.

Demon's Souls didn't do much for me. That said, I may give Dark Souls a shot as I've seen a friend play it and it looks like something I have a shot of getting into.

Only game I can think of that hasn't been mentioned yet is Star Fox: Command. The choices you make can send the story down wildly different paths, though it's not much more expanded than what Star Fox 64 did.

Bravely Default?

I'd advise against putting all his eggs in one basket to begin with. Not only are the chances of him becoming the next Pewdiepie or Angry Joe incredibly low, but there's just no security in this kind of career. If there's one thing that the recent Youtube Content-ID scandal should teach everyone, it's that making a living off playing other people's material is always a risky practice. At any moment, you could have the rug pulled out from underneath your feet and your funding disappear, and it can come from anywhere: a copyright-holder, the site you upload to, your fanbase, or even some random internet trolls looking to make some chaos and/or easy cash. Also, the internet world moves incredibly fast. What's in today may barely have any fanbase tomorrow. He might be able to make a hit streaming show, but there's no guarantee it's going to have any more longevity than your typical teen pop star sensation.

But if your friend still insists on trying to make a living off it, I'd be encouraging him to take it slow. It sounds like he's just jumping right into a practice only because he saw how much money other people were making at it. Does he have any experience in streaming or Let's Playing at all? Does he know how to be entertaining or informative while playing a video game? It (usually) takes a lot more effort than it seems to make quality stream/LP videos, and this isn't even getting into finding an audience who'll watch you, which always carries a significant luck factor.

So yeah, I'd definitely encourage him to go back to college instead of abandoning it for a small chance at some easy money, or at the very least make streaming a hobby instead of his sole source of income. If he does go through with it and ends up failing miserably, make sure to support him and not get all high-horsey about it. As others have said above me, failure is the only way some people learn.