EDIT: I changed the quest substantially to remove the race and crime elements. The quest is now much more light hearted.

Premise: An innkeeper wants you to end a petty feud between two bards at her tavern

Assets needed:
A scripted jug of Spiked Shein that knocks out (Damages Fatigue moderately quickly to 0, perhaps by being twice that of the target’s Fatigue regeneration) on the drinker. The player gives it to the target via dialogue, so it could act when given to that particular NPC as well.
A pair of scripted Shoes that force the target to jump over and over again for a certain duration (~30 seconds). They should also act either on use or on give (to the particular target).

Locations:
An inn
A jail

Characters:
Darayne Llarem, the Dunmer publican of the Drunken Guar Inn
Moreth Helsim, a Dunmer bard in the inn
Rajjma, a Khajiit bard in the inn

Detailed Summary:
The player hears rumors that the local inn’s publican has had enough of two bards’ squabbling. If they travel to the Drunken Guar, they hear it straight from Darayne. Though they both seemed promising entertainers, their bickering has been driving customers away. She is tired of the two fighting, arguing, and constantly trying to one-up each other. She asks you to speak with the two of them to end the fighting, one way or another.
Speaking with Darayne or the inns guests reveals more information about the two:
Moreth Helsim is the youngest son of an influential family who has been using his name and connections to get ahead. He is a lutenist and a talented dancer – that is, he is very Acrobatic – but he is far too serious for his avocation.
Rajjma is a gifted musician who is new in town. His routine incorporates his signature ribald sense of humor – he wows the crowd with Speechcraft – but he enjoys his drink a bit too much to have any stamina.
The player can talk to the two of them to learn their grievances. Each accuses the other of trying to steal the spotlight. Moreth complains that Rajjma makes lewd jokes that interrupt his performances, and likes to steal his shoes. Rajjma claims that he can only get a few jokes out before Moreth starts to distract the crowds with his dancing, and mocks him for his taste in alcohol. 
Each asks the player to help him settle the score with his rival. At this point the player has the following options:

1a. The player can support one of the bards over the other, leading to a revenge plotline. If the player agrees to support one bard, the other will no longer ask for the player’s help.
1b. The player can betray one bard to the other and then help that bard get revenge. This leads to a revenge plotline.
2. The player can betray both bards to the other, ending the quest unless they choose to pursue 4.
3. The player can convince the bards to work together, leading to the reconciliation plotline.
4. (If the player has the official Entertainers plugin) The player can offer their own services to Darayne instead, leading to the usurpation ending.

Moreth’s Revenge
If the player sides with Moreth, he comes up with a plan to sabotage the Khajiit’s next performance. The Khajiit is a known souse, so he asks the player to hand Rajjma a jug of Shein before his performance. However, Moreth will spike the Shein beforehand with a special Orcish liquor, far more potent than the local brews. He tells the player to return to him at the inn at 6:00 pm the next day, which is before Rajjma’s performance.
Starting at 6:00 pm, the player can talk to Moreth to get the spiked Shein. They then have an up to 15 minute grace window during which they can offer the Khajiit the Spiked Shein through dialogue.
If the player does not do this, the Khajiit performs at 6:15 sharp (Intermittently, until 7:00, dialogue windows pop up from the bard telling a joke or humorous anecdote, growing progressively less coherent) and the player fails the quest.
If the player does give Rajjma the Spiked Shein, they watch the Khajiit stand for a few moments before falling to the ground unconscious. Talking to the inn’s patrons about Rajjma reveals that they are unsurprised and mock the bard for his habits. The player can then return to Moreth for a reward, and talking to Darayne also gives them a reward. Returning later, Rajjma has a lowered disposition. He complains of a hangover and admits that he has been defeated by the player and Moreth.

Rajjma’s Revenge
If the player sides with Rajjma, he lets the player help him with a plan to sabotage the Dunmer. Moreth has a special pair of expensive dancing shoes, which the Khajiit stole right after Moreth’s last performance. Rajjma has also captured a small stinging insect, related to the Shalk, which he plans to hide in the shoes. The Dunmer is scheduled to dance the next day at 6:00, and the Khajiit wants the player to claim that they recovered the shoes before his performance.
Starting at 6:00 pm, the player can talk to Rajjma to get the bugged shoes. They then have an up to 15 minute grace window during which they can offer Moreth back his shoes through dialogue. The player claims that they had talked to the Khajiit and bullied him into returning the shoes.
If the player does not do this, the Dunmer performs at 6:15 sharp (He alternates between a dancing animation, preferably not the one from the House of Earthly Delights, and playing the lute – ideally, an animation accompanied by a lute/guitar song playing) and the player fails the quest.
If the player does give Moreth the shoes, they listen to him noticing something moving in his shoe. The player is forced to close the window. Immediately afterward the Dunmer jumps up and down awkwardly for ~30 seconds, after which he runs upstairs in shame. Talking to the inn’s patrons about Moreth allows them to joke and laugh about the bard’s ridiculous antics. The player can then return to Rajjma for a reward, and talking to Darayne also gives them a reward. Returning later, Moreth has a lowered disposition. He is too embarassed to dance in the inn ever again and admits that he has been defeated by the player and Rajjma.

Reconciliation
The player can strong-arm or coerce the bards into making nice and performing together. Rather than by using persuasion, the player does this through dialogue. The player has a debate with each bard consisting of a three-part dialogue tree about the merits of their rival, the shortcomings of the performer in question, and the benefits of a double act. There are three sets of three speech options – a bully option, a diplomatic option, and and an escape option that exits the dialogue tree.
The dialogue tree should look something like this, though more eloquent: 
>reconciliation
RAJJMA: This one does not care for the serious Dunmer. Rajjma does not understand why he does not like to smile. How can a bard entertain if he himself cannot be entertained?
>At least he can walk straight and carry a tune.                                              >Moreth is a gifted musician and dancer.                  >You’re right. My mistake.
RAJJMA: The %playerrace should watch %his/her tongue before                    RAJJMA: Rajjma does not like to admit it, but            RAJJMA: This one does not
Rajjma gets angry. This one needs no music to make his audience happy.     the %playerrace has a point. The sour Dunmer          to discuss this anymore.
And Rajjma thinks it is better not to leap around like a toad.                         can do two things better than Rajjma. Only two.        [EXIT]

etc. 

If the player chooses to exit at any point for either performer, they fail the reconciliation ending. This does not end the quest unless the player has locked themselves out of the others.
If instead the player talks through the dialogue trees for each bard, then the two agree to perform the next day at 6:00 pm. When the player arrives, the performance combines both their strengths – alternating jokes and anecdotes with music and dancing. The player can then collect rewards from the innkeeper and the two bards. 
If the player returns to the inn later, there are more NPCs than earlier, and the two bards are on speaking terms again.

Usurpation
If the player has the official Entertainers plugin, they can talk to Darayne after approaching each bard and offer to entertain the patrons instead. She asks the player to perform the next day at 6:00 pm. The player can perform as in the Five Plates. This results in a disposition drop from both bards and a reward from Darayne, in addition to the performance reward.

Reward:
If the player completes a revenge quest, they recieve a free skill boost rom the bard they helped (Acrobatics for Moreth, Speechcraft from Rajjma) and a special item from each (Moreth’s old [Exquisite] dancing shoes or Rajjma’s copy of A Less Rude Song). They also receive a bottle of flin on the house from Darayne.
If the player completes the reconciliation plotline, they receive a free skill boost from each bard and Darayne will let them rent a room for free.
If the player completes the usurpation plotline, they receive the flin, a free room, and up to 100 gold from Darayne.
If the player betrays both bards against each other, they receive no reward. 
If the player kills either or both bards, they receive no reward and Darayne refuses to serve the player.
If the player kills Darayne, the quest fails with no reward.