You guys have any specific questions? I'm playing through it now and have played Pirates many, many times in the past on PC and PSP so I've already got a sense of how this will go.
It will be a 2-playthrough thing. One on apprentice to get just about everything (the city bombardment with less than 15 cannons would be really tough on Rogue) and then a playthrough on Rogue where you basically try to get to Montalban as fast as possible.
Should be fun.
If the dancing gives you real trouble, you could do a 3rd playthrough where you pick Wit & Charm (makes dancing easier) and try to get the two dancing items and play on apprentice. That's probably your best shot at getting the 150x combo.
I don't really forsee any problem getting all these achievements. Should be real fun.