Hey mate,
Yea many of the options you refer to here are what I do today.
And I know the mod don't upload the dkp again when uploading raid - but what I had in mind as an option was to use the same function that kicks in when an item drops.
in that way you could quite easy have "item members" with a price for a penalty or something.
Don't know if this is an option, but its the best I can think of and imo a similar situation - just with out the item