Foreword

For those who watch my let's plays and livestreams, you'll know that we're all about role-playing and not at all about min-maxing. This series is not about the ultimate [insert class] build, let's face it, sooner or later your character will be a god-killer whether you min-max or not. In addition we tend to always want to play the same way, with the same style, the same weapons, the same game play. So instead, I want to suggest ways to play a class and mods that can make the experience fresh and more unique. For more general role-playing mod recommendations, you can check this guide.

Skills, Race, and Birthsign

For the Rogue, we are looking at personality and speed. The governing attributes for the rogue's skills are indeed, first and foremost, Speed (3 skills), followed by Strength (Long Blade and Axe), Personality (Speechcraft and Mercantile), and Agility (Light Armor and Block).
The male Dunmer stands out with excellent Speed (50) a well as good Agility and Strength (40). If you want more hitpoints at level one, go with the male (Endurance 40) but if you want to be more likeable (Speechcraft and Mercantile) from the start, choose the female (40 personality). Either way, you'll enjoy a nice buff in your Light Armor, Long Blade, and Athletics.
If you prefer your rogue with an Axe, better armour, and less charm, pick the Nord: Your Agility will be low (30) reducing your chance to hit, but with 50 strength, when you do, it will hurt! You'll also enjoy a +10 Medium Armor. The only way you can improve your Agility (chance to hit, chance to dodge, max fatigue, and stagger resist) is to use a shield.

A useful birthsign for the fighting rogue is the Warrior. The Lady (Endurance and Personality) is, as ever, a prime choice.
Personally, I like the Serpent because it's fighting dirty and it fits the rogue.

Gameplay and Mods

For the sake of this guide, I'll consider the Rogue a criminal, very much interested in illegal, profitable activities. For the lovable rogue, you could check the Bard Guide or the Thief Guide. (will be publish 25/12/19)

Crime pays, or does it?

You are being robbed by Arcimaestro Antares, lets you put on a mask and attack travelling NPCs. For better effect, be sure to install mods that add friendly NPCs on the roads: traveling merchants, SF NPC addition or MCA.
Vvardenfell Footpad by Fliggerty handles the highwayman robbery differently, comes with a couple of nice features such as letting NPCs greet you even if you are sneaking.
Go to Jail by Arcimaestro Antares: part of the thug's life, well, the less able thugs.
Wanted Posters by Gavrilo93 and Caeris. Famous at last!
And with fame comes Bounty Hunters by Arcimaestro Antares. They will find you and attack you in inns and in the wilderness.
Fake Gold by Danjb. Buy cheap fake gold from Habasi and hope traders are none the wiser.
Hide the Sugar Hide the Skooma by Rot: you might be a thug, but you are smart enough to put your drugs away when you go shopping.
Or use Advanced Bartering by qqqbbb that lets you barter with skooma in your inventory but will alert the guards if you try to sell it.
Speaking of guards, install Insta-arrest by King Feraligatr. Guards will force-greet you when you walk close to them, as opposed to arrest you ONLY if you talk to them.
No one is anove the Law by Red Furry Demon and Gavrilo93 where contraband is taken from you by guards whwther you stole it or not.

Moonsugar and Skooma

Create Skooma by Merlord, lets you make skooma based on your alchemy skill.
Moon Sugar Plantation v 1.4 by Danjb where you will find both moon surgar and a refiner to make skooma.
Khajiit Dens by Dbfuru. A place to bring your customers maybe? There is a skooma dispenser for personal use: the bottle has a 0 septim value because you can get as many as you want.
Vvardenfell Druglords by Fliggerty. THE mod for the dedicated drug maker and drug dealer. You will need quite a lot of money to get this business going!
Adanumuran Reclaimed, my own mod that lets you take over a smuggling operation and develop it by bringing in illegal goods (moonsugar, skooma, dwemer items, ebony). You may sell them for instant profit or invest in your business. Comes with a skooma lab, poison arrow crafter, alchemy sorter, training dummy, displays...
Skooma Dealers by Merlord lets you sell skooma to Khajiits and sketchy traders. Balanced: the price is based on your stats.
Thieves Guild Fences by Melchior Dahrk. These fences will buy everything.

Combat

Apoapse's Alchemy is a mod that lets you place traps with any potion in them. The content of the potion (preferably a deadly one) will be released as soon as an NPC walks by the trap. Hint: install Poison Crafting by Greatness7 and start collecting those chunks of corprus meat. Naturally, Poison Crafting alone lets you coat your blade with poison. There's just something about traps that feels so... devious.
More ways to fight dirty, try Arcimaestro Antares' Oil Flasks and Venefic Vials with the same idea: drop things that hurt.
Fliggerty's Booby Traps, same idea, different effects.
Check the Assassin Guide for all kinds of sneaky backstabbing trickery.
Want something a little more flashy? Aftershock's Flintlock Beta adds a proper flintlock pistol and a mold to make ammo. Currently not in-game but I've made a quick mod you can find here that puts the pistols and the mold for sale at the Razor Hole in Balmora.

Criminal Factions and Houses

Thief Hideout by Auric. A discreet lair for the rogue in Balmora. Even criminals like a bit of convenience. Grab MWSE Containers for extra storage options.
A little further away, try Balmora Cave Hideout by Vicart: a somewhat large cave with storage and display space. I'd recommand a furniture mod so you can add crates and barrels.
Smugglers Peak by AlexMercer984 for the smuggler who likes fresh air and a quiet place. It's more an open-air hideout than a home. Still looks great!
Make money bringing slaves in with Nevena's Twin Lamps & Slave Hunters.
Errands for Orvas or Join the Camonna Tong. Good to get you started until you can run your own operation.
Dura gra-Bol's House Reclaimed by Melchior Dahrk. It's a house, it's a faction and you get to do shady business. You want this.
Black Tooth Pirates by ChemicalTaint, even better with Pirate Outfit by Mandaramus.
Treasure Maps by qqqbbb. Why risk your hide stealing or killing when you can just find treasures?

Handicaps and Goals

Commit to your career, no time to save Vvardenfell. Select your factions wisely: Thieves Guild, Fighters Guild, House Hlaalu have goals that align with yours. In fact, you might consider joining the Sixth House, I hear the Ash Statue business is lucrative.
Recruit known bandits and criminal from the game to make you own gang: Nels, Fjol, Velfred, Pemenie... You will find many smugglers and slavers in caves and the Camona Tong has its fair share of thugs. Make sure to have the means to calm them first, then to recruit them: Supreme Follower System lets you tell any NPC to follow, wait to take your place as well as share inventory or NPC Functionality by Casey Tucker lets ask any NPC to follow, guard, report on their health, skills ans spells. NPCs will agree to follow based on your level, speechcraft and their disposition.

Final words

If you want more ideas for random handicaps and goals, check this blog entry with wheels to click, you can find my permadeath modlist (and all the others, actually) here and if you'd like to see many new characters created, join us on Twitch every Sunday for our permadeath runs ;)

Happy Morrowinding!