Idk, zeppers is probably right, it's either a glitch or they lowered the max level cap. (I doubt it though)

They havent lowered any max level caps.

When I first suggested that exactly what was level 5 (notoriety or weapon) wasnt established.

Seeing now he says hes Notoriety 9, and doll level 5, I haved no idea unless its the level of enemies hes attacking.

Ok. I think I know what's with Big D. They don't want players to go too far by getting both guys weapons cap to 7. so your first guy can lvl all your weapons to 7. But Big D doesn't want people to prepare by having the second guy able top go to 7 on weapons so they made the second cap to 5. Heres a table...

1st

Cannon-7
sailing-7
Cutlass-7
Pistol-7
Doll-7

Second guy only gets those to 5...

I also think they give little special features for basic people. Because I lvld my first guys weapons long ago and was able to get the stronger versions of weapons. Now they don't let us get them. But we can start right up without having to wait. :)

I just created a second throw-away pirate - it is positively still getting cutlass points AFTER level 5. You need to attack yellow and red enemies, not gray enemies. You can't just automate Hack Slash Cleave and attack level 1 gravediggers...

Actually all the weapons can be leveled beyond 5 except for the doll, the doll is stuck at lvl 5.