Maybe he didn't want to be pro cause he knew inside he wanted to leave Primitive. Being pro and leaving is far worse than leaving as an AM.....no?
That's a good point, I don't think it would be a good career move to be in the bad books with the Rodfather. Regardless of what you think about him, you can't really deny the influence he has on the game. It would be a really bad look to go pro on there and leave etc. and maybe he was just honest with Paul and said he has bigger ambitions than primitive which is pretty reasonable considering he is kind of a "once in a generation" type skill level.
I also think its fried to assume he is not doing fine with his sponsors financially

i dont think he is in any sort of rush to do anything which is pretty rare for skateboarding, sounds a bit like the janoski story where he turned down an etnies pro model - he likely also had the self awareness to understand how mcuh his "brand" was worth at the time. From what I have seen, he seems to be an intelligent human being.
People need to stop getting so caught up on the title of "Pro" as if it means anything more than a Marketing scheme to sell more boards because it has a guy's name on it. There are children in Japan and Brazil who you can probably ollie over who are already superior skill level to even most of today's Pros. I think that is kind of looking at things in a vacuum when you say "well so and so has a board so why doesnt Dylan".
there are definitely plans for that guy to have a pro board with his name on it and everything is a profit maximization strategy ultimately, the timing just has not been there. If you consider in previous generations, it was a revolving door, so they had more room to turn people pro more often. and also the pay was so non existant as an "am" no one would turn it down just to survive. Most companies dont really do "Ams" anymore. its just flow to pro.
the big companies have a ton of guys over 30 on your team with families and shit now. it is a completely differnet landscape. there are more legacy / legend status type pros as that sort of roster grows too. Element had like 30 pros for awhile. people clowned on it but they were keeping a lot of pros afloat who would have otherwise just did construction and fell off