I've played Skyrim for several hundred hours on my current character. During that time, Ri'saad went missing, presumably dead. The rest of his caravan NPCs continued to roam about without him, and when at their Whiterun trading location, they would never set up camp, but stood around exchanging their scripted dialogue instead.
However, since joining the Thieves Guild, Ri'saad has respawned and his caravan now behaves normally. I presume he's been resurrected as he is required for one of the TG quests. Either he's been dead and resurrected (as happens to some Companions NPCs) or the game glitched and simply failed to spawn him, and joining the TG sorted the glitch out. Evil-i (talk) 22:47, 7 October 2014 (GMT)
Another Solution Found?
As of completing Diplomatic Immunity, and helping Malborn get out alive, I was surprised to find a similar if not identical situation to the previous post, however since I had a save before the "bug" occured I could ascertain down to the exact quest that caused it and why.
Immediately following my escape from Reeking Cave the second time through after discovering the "bug". I immediately fast traveled to Windhelm (as per the note in the subsequent article) and saw that, somehow Ri'saad and his entire entourage had joined with the caravan of Ma'dran's which I didn't understand until reading the "Find The Thalmor Assassin" sidequest of Malborn's.
There is apparently a unique line of dialogue Ri'saad provides to point out the assassin. Which is presumably why he diverts his course from his usual Markarth to Whiterun route to that of the Windhelm to Solitude. The effect on the quest makes the stage update to an arrow pointing at the assassin/'s location where before the directions Malborn gave you were simply ambiguously "Find The Assassin".
However, this piece of dialogue could completely be missed, by arriving at Windhelm when Ma'dran/Ri'saad and Co. aren't there (Most likely at Solitude) since in this case there would only exist one conspicuous khajiti assassin, not being part of any caravan at all, the player can immediately ascertain they are the assassin before the game developers intended and kill them. Presumably, this "bug" wouldn't happen if Malborn dies during Diplomatic Immunity, or a troll or other wildlife gets Malborn before he arrives at Windhelm.
One final note about completing the "Find The Assassin" quest. Once Malborn gave the reward for a quest complete and presumably booked it to the border with Morrowind. I noticed Ri'saad resumed his normal route (by which I happened to witness by exiting Windhelm, and viewing his entire group pack up and leave). Upon Fast Traveling to Whiterun, however - for whatever reason, despite his resumed appearing with the other three Khajiit in their proper locations outside Whiterun gates - they would never set up their campsite in Whiterun (I tried waiting several hours, and reloading the cell by going in and out of Whiterun, which usually does the trick). However, upon fast traveling to Markarth, and observing them erecting a campsite there, and then immediately travelling back to Whiterun they began to make the campsite again.
As of writing, I am unsure whether or not killing the assassin without talking to Ri'saad whatsoever, may quietly fix the bug even without the player noticing. CannotIntoEdits (talk) 04:04, 13 September 2016 (UTC)