Personally, I agree that we should have the option to Re-Roll our pirate, but in a different way than this topic suggests.
Instead of a Re-Roll, I'm of the opinion that all players should be able to buy a second character slot. This slot is tied to your account, so no progression is lost, but you have the freedom to play as a totally different pirate than your first one, and would now have the option to delete it if you so choose.
I'd say that your second pirate should share gold, reputation, and overall progress, but not share doubloons, commendations, cosmetics or ship customizations. This way there's still something worth working for on this second character, but you don't have to grind it out twice either.
I think a buyable second character slot would be the best of both worlds.
I'm in agreement that we should be attached to the pirate we first chose, as it makes us work a little harder to get them through their trials to become legends. That said, as much as I love playing as my tough as nails, skinny and aggressive looking pirate lady with a taste for nice cosmetics, I'd still like to have the option to play as someone different from time to time.
It'd be nice to have other things to buy cosmetics-wise, and have a whole different approach to the game on a totally new character. Hopefully rare considers adding this as a feature, as even if it's a microtransaction, I'd be happy to pay for this one in particular.