My 4th pirate Sophitia Swordrage ended up being my 1st one to hit 40 on Oct 20th... did desolation + wither caused a bit of lagginess so my screenshot f9 command didn't go thru quick enough blah oh well. Sophi had sailing + all weapons mastered by the end of 38/beginning of 39, cannons at lvl 19 was all that was left. Went to KH when I needed 8 more rep to plunder a random treasure...
My 1st pirate Angel Daggerfury, the one I kinda gave up on at lvl 37 for a while, finally got to 40 on Nov 11th... check out my nades =P Was trying to master Angel's nades before 40, but ended up getting rep from other weapons. Angel had sailing + doll mastered, cutlass 23, gun 20, dagger 19, staff 24, & cannons 22.
A guildmate, Chris Darkskull, mastered on Dec 3rd while cannoning... missed his glow by seconds tho. He's got dagger, cannons & nades left.
Edit: Also, Ben Seagrim (June 22, 2008)'s 2nd lvl 40 is Gentelman Jack (Nov 1, 2008), 3rd lvl 40 is D'artagnan mastered yesterday (Dec 7th)