Why are so many people pretending to be so naive about the point of all of this?
Highlighting Gibb's family's standard of living, education, occupations, and his upbringing isn't to somehow denigrate those achievements as being lame or an indicator of being soft. It's to illustrate the ridiculousness and stupidity in championing the exact opposite of that lifestyle day in and day out in your music. It's cosplay-esque behavior.
Cats really tried pulling the dap fishing card of "why is it only black people that view being educated as a negative?" in something as plain and cut and dry as this?
The point is Gibbs looks silly playing the superthug role raised in such an environment. That's all. I don't see how it's even possible to read into it any deeper than that.