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If you let the hidden 24 hour timer between arriving in Windhelm after Malborn getting there, and Ri'saad's caravan returning to their old route, run out, you will be unable to speak to the assassin, preventing the quest from progressing.
Killing J'datharr will advance the quest. If you don't want to just attack him in cold blood, cast Frenzy on him; even if his level is too high to be affected, he will turn hostile, allowing you to kill him and continue the quest.
You can circumvent this by opening the console and entering setstage MQ201Malborn 30. This will place a quest marker on the assassin and allow you to talk to him. After picking "Malborn has a message for you." he will turn hostile and you can kill him normally.
The Khajiit in Ma'dran's caravan may not tell you about J'datharr being the stranger in the group, meaning you can not talk to him to send him a message from Malborn. Reloading does not fix this, nor does pickpocketing the note from him.
Killing J'datharr will advance the quest.
EDIT: The reward is only 50-250 gold, depending on level. There are no follow-up quests that you will lose out on.
Hey, that worked great. Thanks for helping out.