I don't think he will get a major shoe company to sign him. I think many would be skeptical about putting on a guy with his criminal record, which involved an assault charge where he could have potentially injured a minor. People may say someone like Daryl is still on Nike, but one, he wasn't convicted of anything, and two, they weren't aware of this when they put him on contract. Most likely, someone with Daryl's current reputation wouldn't get on Nike regardless of their skating (there are questionable things about Nyjah, but none to ever hit anything past the message board, Daryl has a vocal accuser).
Now, I do think if he cleans up, he could get on something semi-legit that could pay him like Emerica, Lakai or DC. I just can't see Nike, Adidas and NB# putting him on. No idea about Vans, but I'd lean to they'd avoid.
As for board brands? If he puts out a comeback part that is up to the standards of pros his age with the same classic style, he'll get a board on something legitimate. Whether its being back on Baker Boys or someone else gives him a shot.