I was thinking of making my rogue go through bard then straight to assasin, or maybe ninja to assasin, not sure. Can more than one character become a samurai/ninja/etc in the same group? Quest-wise I mean.

I've been using a twist on the character transition strategy made famous in Wiz7.

//As you remember W7 had unlimited visits to classes so you could pick out two
or three that worked well for a particular character and bounce back and forth
gaining skill points along the way.//

Well in WW, I am prgressing through classes and plan to get through all 8? and end
as an ascended character class.

My party has six members and a for instance on this progression is:
Rogue>>Bard>>Samurai>>Ranger>&gtaladin>>Warlock>>M onk>>Ninja>>Assassin

Don't know whether I'll get all the classes in or just punt at the end...
Depends on my interest level and ready supply of exp. points.

Just keep the skill bug/cap in mind. You cannot scroll skills once the box is filled.