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 Agent class, Agility and Personality are the main attributes and looking over the skills confirms this, but speed is also quite important and will progress quickly thanks to Short Blade, your main weapon skill.
Agility will increase using Light Armor and Sneak while Personality increases with Speechcraft and Illusion.
If your Agent relies more on combat that deceit, the Khajiit is pretty good: top Agility, and decent Personality. With their high speed, you'll be in and kill and out in seconds.
If you want to go the Personality route, Imperials seem an obvious choice with high Personality and +10 Speechcraft. Be careful, though, their Agility is quite low (lower hit, less dodge, more stagger), and they have no talent for Illusion.
Personally, I like the Altmer for an Agent. The Dominion is not yet ready to take on the Empire but is scheming, nonetheless. They need to know what is happening in Morrowind: anything that might weaken the Empire is good for the Dominion.
Be a Thalmor Agent, long before the rise of the Thalmor!
In addition, Altmers have 40 in Agility and Personality and +5 Illusion, female Altmers also have 40 Speed.

As for birthsigns, The Lady is great (admittedly one of the best birthsigns regardless of class) with a nice boost to Personality. Keep in mind that the 10 points of Endurance doesn’t go towards your starting health. The Lover is a good choice as well, especially if you play a female, The Lover's Kiss is just the thing for a lady-spy.

Gameplay and mods

The Agent is meant to operate, more or less, secretly and in favour of (a) given faction(s). Favour Speechcraft to taunt NPCs if you need them dead, Illusion to calm them to extracted necessary information from them or if you simply changed your mind about killing them ;)

Faction mods

There are very few mods that let you work against a faction, but quite a few to expand certain ones:

• Stuporstar's Uvirith's Legacy A must if you are joining House Telvanni.
• Caldera Mine Expanded a quest mod that will let you choose an outcome favouring a Great House.
• Errands for Orvas or Join the Camonna Tong Since the Camonna Tong operates illegally, you can work secretly for them. The former mod is more lore-friendly and the later only accepts Dunmers.
• Grandmaster of Hlaalu will let you expand the House's power. Achieved, however, by not actually working against other houses. Warning, the mod is large and has a few minor issues.
• Brother Juniper's Twin Lamps Put your skills to good use for the good of freedom! Free the slaves using open spells and/or lockpicks (Mod by Caeris).
• Great House Dagoth Because even Ur deserves an Agent.
• Rise of House Sadras by RubberMan and RubberBoy. This large quest mods adds a whole new faction.
• Vvardenfell Brotherhood by Caeris lets you join the Dark Brotherhood.

For the Imperial Agent (as in, serving the Empire):

• Imperialist Nerevarine Lets you stay true to the Empire and makes it so that you do NOT have to join the Ashlander faction.
• Imperial Legion Expansion to bring more law and order to Vvardenfell. (both mods by Gavrilo)
• Imperial Contraband to turn in illegal goods you’ve confiscated. If you want to arrest NPCs who violate the law, put Archimaestro Antares' Big mod to use.
• Imperials go home lets you deal with anti-Imperial graffiti.
• Blades Quest: Prophecy of the Lost Heir by Emma. A large quest mod where you continue serving the Blades after the main quest. Be sure to have Melian's Teleport Mod or the newer Customizable MWSE Multi Mark and Harder Recall as the companion scripts are a little dated (early Grumpy scripts).
• Increase the Empire's influence through its exports, and make a profit with Import Business; the Merchant of Vvardenfell by Psycholex.

Finally, I like the idea of an Agent representing a faction OUTSIDE of Vvardenfell, leaving you free to investigate the powers of Vvardenfell as you see fit: Your character is interested in politics? Join all (3 Great) Houses Essentially, you are free to join any faction, either because their goals align with yours, or because you are working to gather more information on them.

Other mods

• Give a gift by NullCascade: otherwise known as, the art of bribing!
• The Last Witness by NullCascade: a must have for the efficient Agent: you might need to kill but you don't want any unwanted attention!
• Take Notes by qqqbbb: to write down those coded messages or MWSE Journal and Search Edit by Sveng: to keep your notes in your journal. On the plus side, you can add images to your journal.
• Brutal Backstabbing by Merlord: multiplies damage as long as you attack from behind and with a short blade (configurable).
• Advanced Persuasion by Danjib: beg and threaten using your Speechcraft.
• Get that special hood for missions from Ninja Outfits in Molag Maar or go with the scripted Thief's Disguise by Max, lets you buy face paints.
• Assassin's creed armour by Weslty, for sale in Caldera (I'd go for the darker colours).

Chargen mods

I'd recommend Class Abilities that lets you pick a profession independently of your class though all vanilla classes are there as a profession.
You can of course choose the Agent, which gives you a couple sneaky powers, +10 Sneak, as well as a Jinksword, a Lockpick, and a Probe.
I personally like the Shadowmage that gives a +10 Illusion, especially if you chose an Altmer! Your Illusion should be high enough that you can start charming, calming, and blending into the shadows straight away.
As always, Merlord's Character Backgrounds: this mod doesn't just give you items or powers, it actually influences your gameplay and CREL because it should be on every modlist.

Handicaps and goals

• A good Agent is one that doesn't get caught: may I suggest game over if you are arrested? To make this an actual challenge (we all know how dumb guards can be) either go for insta-arrest by King Feraligatr where guard will force-greet you as soon as you approach them while you have a bounty, or for a greater challenge, try Sveng's Pursuit Revisited where guards will actually come from nearby cells as soon as someone reports your crime. Warning, this mods is quite a challenge! Oh, it also lets you lock doors with lockpicks. (not compatible with The Last Witness). If that's too much, then install Go to jail to make the experience more fun.

• Try to stick to Illusion spells: Charm, Chameleon, Sanctuary, and Paralyze are great in the Agent's arsenal. Hurling fireballs… not so much :)

• The Agent dabbles into Conjuration: stick to the Summon Dagger spell: the ultimate concealed weapon is the one you are not carrying!

• Goals will vary with your narrative of course, doing missions for your chosen faction(s) is one thing, killing the leaders of opposing factions is better! You may do the deed yourself or… you could pay the Morag Tong to do your dirty deeds for you, using Archimaestro Antares's Superb BigMod a must-have for any gameplay; in my humble opinion.

• You are after information: be sure to steal all notes, ledgers, and reports you see.

• Keep tabs on prominent NPCs by tailing them. Install either Dopey's npcs or Living Cities of Vvardenfell to let npcs change locations. With Dopey's mod, NPCs will simply go home (lighter scripts), with LCV, they will also go out for a drink, wander around the guild hall, etc (heavier scripts).
  

Final words

If you want more ideas for random handicaps and goals, check my blog entry with randomized wheels to click, you can find my permadeath modlist (and all the others, actually) here and if you'd like to see one of the many new characters created in action, join us on Twitch every Sunday for our permadeath runs ;)
I would love to hear how you like to role-play as an Agent~