Which Pirate Should I Level?

[Juliana Maria]

I'd have to say Shadow if your going for 50. Like you said, he hasn't missed out on rep yet. Where as James has done all quests etc.

[Basil Dreadflint]

I think they both can get to 50. But the one that still has some pre-update rep to eran will have an advantage over the one that finished a lot of stuff after hitting 40. The rep/no rep cut line of level 40 means that anything done after reaching 40 isn't going to count towards reaching 50. At least, that's the way it appears right now.