Not having a manager, dropping that streak of bad albums, being inconsistent with release dates, choosing the side of the crackhead when sgp vs asap mob was a thing which hurt in the long term since the raider klan fell apart, pretending your pops isnt your pops, not in xxl freshmen list when it meant something, and doing all of this stuff independent will do that.
He did have a manager. Same manager as Pouya's when they were a part of that $mart $tunnas thing. What hurt him more was being too d***ged out and failing to capitalize on Tha City. He only dropped a handful of tracks sporadically between 2013-2015.
What streak of bad albums...?
Inconsistent release dates is fair
ASAP Twelvvy, Bari, and I believe Illz started a fight with dudes in Raider Klan and one of Robb's homies. Robb had beef with Meechy Darko and Underachievers (Tumblr s***). Yamz got involved, which led to the reveal of Shaggy being his dad. Led to a spat between Robb's crew and Rocky's crew at an airport. I'm not really sure what or whose side you expected him to take in this situation.
With the way people often don't take nepo babies seriously, it would've been the same thing to happen if he was going around saying he's Shaggy's son. If anything, he'd have that plant label thrown onto him, which probably would've hurt him more. We ain't gotta lie about this one.
Could've been on XXL Freshman around the time of Tha City, but again bullshitting around on d**** hurt that chance. At some point he chose to not do it because he felt his time passed and he didn't want the focus being about him being Shaggy's son who raps. Kinda valid.