New challenge inspired by Jiub's life and death.
I used the UESP page on Jiub as a reference.

Character Overview

Lore #1

Jiub was originally a freelance assassin, who murdered to pay for his skooma addiction.

• One-eyed, bald Dunmer male
• Assassin Class
• Do not join assassins' guild(s)
• Must consume skooma regularly: depending on your gameplay, it could be once a day or every time you rest.

With mods:

• Quick Char v1.2 by Bink & MaXiMiUS to skip that awkward moment with yourself in the boat
• Texafornian's excellent and more complex Chargen Revamped - Expanded Lands gives you multiple starting options.
• Merlord's Create Skooma lets you make your own skooma with moon sugar and a skooma pipe. Success depends on alchemy skill.
• The Bare Necessities by Desctructor and tweaked by WanderRA: optionnal skooma addiction

Lore #2

Jiub, wanting to make up for his dark past, sought redemption by serving the people of Morrowind. He made it his mission to eradicate the Winged Menace, the cliff racers who plagued the roads of Vvardenfell.

• No killing people unless in self-defence (no taunting either)
• Hunt Cliff Racers to extinction: kill 200+ cliff racers.

With mods:

• Jaxalo's Hunt Cliff Racers to Extinction: by default, you need to kill 200 cliff racers
• My own Cliff Racers that introduces a variety of cliff racers, each breed needs to be hunted separately. Cliff Racers now range from level 1 to 80. Includes a report that keeps tracks of how many birds you have killed.

Lore #3

It took years to hunt them all down as he travelled Vvardenfell atop a silt strider, but in a final battle in the ash wastes, Jiub was triumphant. Vivec, admiring his virtue, saved Jiub from death and brought him to his palace, where he was made a saint.

• Only travel on foot of by Silt Strider. No guild guide, no teleportation spells.
• Vivec will not canonise a heretic: complete the Seven Graces and collect all 36 Lessons of Vivec.

With mods:

• Abot's Silt Striders lets you enjoy scenic trips when taking a Silt Strider.

Lore #4

Jiub later moved to the Cyrodilic city of Kvatch, where he began work on a twenty-six-volume epic to serve as his autobiography.

• Gather 100 sheets of plain paper in preparation for your epic.

With mods

• Inscription 2.0 by Lap and TheDopeHatMan lets you create paper with the right ingredients.

Lore #5

Jiub, who was writing in his house at the time of Mehrunes Dagon's attack, was soul trapped by a Dremora.

• Inexplicably, Jiub is uncomfortable around soul gems and refuses to use them.

With mods:

• Merlord's Character Backgrounds: Blood of Dremora where you can be attacked by a Dremora when you rest.

To sum up

Chargen

One-eyed Dunmer male
Assassin class
Optional: Merlord's Character back ground, Dremora Blood

To win

Destroy Cliff Racers
Collect 100 sheets of paper to write your 26 volumes epic memoires
Read all 36 Vivec's sermons.

Handicaps

Only travel on foot or by Silt Strider
Drink skooma regularly
Never use Soul Gems to recharge an item, make or have an item made

Variation

You can elect to be Jiub's faithful companion and help him in his quest.
With mods like Outlaws or CM Partners, Jiub will be a companion.