you need a certain amount of like with him and he'll give it to you. just keep spamming his quests and while doing it he should eventually give them to you. you can also cheat them in but I don't know what that might do...
Hello sir, can you help me with the Northcrest conspiracy and Orc's war? It's just that I can't seem to proceed I am sticked with the quartermaster arranging a meeting with me and lady Tess. Am I supposed to wait or something? Also I've been interacting with NPCs in Northcrest too.
90% certain the meeting hasn't been added yet. he says he'll set it up but that hasn't been added in game since Lady Tess also hasn't been added. so I believe your caught up unless I'm forgetting something.