There’s almost no question in my mind Gloom Management put Steezus up to asking for more bread.
Given his ties to Crail, I’m guessing Edly was fine with minimal to no pay for sitting through the Experience. But I’d imagine the lack of interest in Number Thirty Three after years of promoting it on the show, paired with Kelly’s conspicuous coupling with the very shoe brand that broke up with him, to effectively end his time as a paid skater - had more to do with his discontent.
I love how they waited just long enough for Steezus and Justin to start their new things before “deciding” to reboot the show. Just too good.