http://bugs.winehq.org/show_bug.cgi?id=19449
--- Comment #3 from William J May may.11b@runbox.com 2010-03-09 02:04:16 --- I tend to agree with ejwaxx, this sounds like a game bug- not a Wine one. KOTOR2 is known to be VERY buggy, especially when it comes to completing specific quests. Even the official 1.0b patch only addresses a handful of the bugs to be tackled for this game.
Do you have access to a Windows install where you can copy over your savegame and verify that it succeeds there?