I like the tracks that mix things up. Frank Ocean + his new track of Life of Pablo (thank god Ye split that into a sep. track instead of leaving it as a hidden track built into another song originally) Ghostpoet's Survive It is a great touch.
Mapei's Don't Wait is great. The Nosaj track that Cudi sampled.
Some great less than mainstream bangers too like Kendrick's Backseat Freestyle and Vince Staples. Mos Def Sensei on the Block. Joey Badass' Paper Trails. ASAP's r-Cali.
I wonder if you should make Mick Jenkin's Jazz the first track. It kind of represents the vibe of the entire playlist as you describe it.
Best track tho is probably Bill Bev Devoe's Poison
Could use some grooming - seems more like a go to archive of your favs (something I do too) - but all in all some great hidden gems in here.
I've been tidying my list up a bit, so there is more of a mix (for the first 100 tracks on the list). You maybe should take a quick look at it! I will do the others later on, because the finals are coming up, and I don't have that much of time the next three weeks!