"Machiavelli" (2Pac – Tradin War Stories) | pending

Yes, Makavelli is his nickname BUT the OP is correct because Tupac read about him when he used to live with and visit his aunt in North California and thoroughly examined his work while locked up in Clinton Correctional.

"Ain't nothing on this earth will make a nigga like me stay" (2Pac – Tradin War Stories) | pending

Actually, he converted while still with the Outlawz. The first verse of “I Ain’t Mad At Cha” is dedicated to Napoleon.

"Thug Life" (2Pac – Tradin War Stories) | pending

It’s both, he explains the Acronym on his first two albums along with several interviews and then names the group with he, Big Syke, Mopreme, Machadosis(Mac-10), and Rated-R under the same moniker.

"Pretty boy niggas frontin' hard is the issue / Word to my..." (Mobb Deep – The Start Of Your Ending (41st Side)) | pending

Havoc, not Prodigy

"Well, where I'm from, we like to ride on foes" (C-Murder – Down 4 My Niggas) | pending

they dont ride big rims out west and judging from the next line, he does mean foes, since he says he’ll take em out aiming down the sights of a gun he has to balance on his shoulder or straight up fist fight toe to toe.

"Stay low key like midget doorknobs / Stay above the law l..." (Ras Kass – H2OProof) | pending

If she’s giving blow jobs, you assume she’s kneeling down and he’s standing up thus he’s gonna tower over her during that time

"Little do they know, your girl grill harder than / Some o..." (Mase – Lookin' At Me) | pending

He’s saying that the girls willing to stand up to conflict more than their man. Grill was slang that got replaced by mean muggin when you you had a stare down, grill highlights the emphasis of clenching and exposing the teeth in anger

"Let my pants sag down to the floor / Really do it matter ..." (Mase – Lookin' At Me) | pending

so random and Obama wasn’t even that prominent in opposition to rap music/trends especially in the late 90’s

"And if it wasn't for this Bad Boy exposure / CD, TV's, re..." (Mase – Lookin' At Me) | pending

He’s saying, if he wasn’t popular, would there even be an issue with people flocking to him and causing him all this trouble?

"And if you got a girl, don't be real committed / Cuz Mase..." (Mase – Lookin' At Me) | pending

Could be referring to the Arion girl he mentions later in this album that Dame Dash was going to fight over for her ex-boyfriend on Roc-A-Fella’s team