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Hey I can't do the tasks for Finnegan in the Dockgrave Tavern. I spoke once to him for the first Task and now the "Need Slaves" option is greyed out and I can't turn in a fitting slave. Am I missing something here or is it a bug?

It got changed in newer version, once you start it, girls can be taken there by action->task & location, same menu you now use to take them to Nika's, Watery Eyes, etc. If she meets requirements you can sell off that menu.