To save your save game files u which includes all you characters and exp, weapons etc , u need to save the "save" folder and the "mpsave" if u have any multiplayer games u want to keep. To just exported characters then u need to save the "characters" folder.
And finally if u don't play IWD through again when u have installed HOW then u will! miss out on a lot of new stuff!! so yea u realy need to play it again , damn good game made better we realy can't complain . And I can't answer you questions on dale keeper cause I've never used it. Any questions on shadow keeper I should be able to answer though.
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