I went to the Pearl and tried to beat Isabela at cards so I could be taught the Duelist skill. Turns out my DEX wasn't high enough, so I decided to come back later once I'd upped it. I've returned to the Pearl several times now, and she's nowhere to be found. Does she eventually return there, or did I miss my one chance to make my rogue a duelist?
"Fear is the oldest and strongest emotion of mankind." - HP Lovecraft
Catching Isabela at cheating may be random, actually. I tinkered with her dialogue and at one time I managed to catch her at it after the first try and afterwards it took me 3 tries. The Dex check may be for the dialogue option to appear, however.
'Sonny, what's the name of that nasty German who keeps hiding my stuff from me?' 'Alzheimer, grandpa.'
What I do when I play her is the first time you're presented with the option to try and catch her or continue playing select continue playing. Then it will be presented again, and that's when you try to catch her. I had to do it twice and it worked both times
I don't know why she isn't there though, I beat her the first time (both times I had to do it) so I never had to go back. She's the captain of a ship, try going to the harbor and looking there?