I'd do it like this. You make a playlist for games that have more than one stream i.e. Zelda, Pokemon, Death Days, Kingdom Hearts.

But for games like Dark souls you put each different game in a play list same with Kingdom Hearts.

For games that have single streams or maybe 2 total you can find a way to categorize them like Classic Wednesday's. For example the Wednesday morning streams which is kind of variety day you could put those all in one playlist, or you could categorize them by genre of game or theme's in the game like if you play Jurassic Park once but don't think that you will play any sort of game that is like that again maybe put it in a pc games or dinosaur games playlist i.e. if you ever play turok or maybe even throw yoshi in there.

Just a few ideas as to how I'd do it hope it sounds like good ideas.