I just started a character named 'Niles Dubose,' a Dark Elf Assasin-type character who is a 'solution-for-hire' type. 'Niles' is new in town, as I am new to the Dark Side of RP. I figure that 'Niles' is going to start doing the Mages Guild right away for access to the Arcane University, but once he is granted access, probably have a change of heart and stick to the morally corrupt guilds.

What's your advice on how I should go about starting my life of crime? I've only ever played chaotically good characters (well, at least Neutral), so this is a bit of a strecth for me.

Thanks for the help. I've created a custom class, mostly play based (not into the whole 'efficient leveling' thing.) 'Niles' prefers clothing to armor, prefers Destruction magic to weapons, but works with Blade and Blunt. He will only ever use a shield for armor, no other armor just clothing. He seems to have been a Bard in a previous life as he speaks with everyone he meets and tries to persuade them, but he's getting easily ticked off.

XBOX 360 GoTY, no DLC.

I'll keep you updated, but want ideas. Thanks!

I guess you could go through the Mage's guild quests until you have an encounter with someone dealing in black soul gems, or maybe a vampire. These would both be good opportunities to see the darkness and turn from his path of light.

Speaking of Mages Guild recommendation quests, I find that rogue mage, Earana (Chorrol) irritating enough to entice any latent assassin tendancies right to the surface. . . . Conveniently of course, she is not a member of the Mages Guild.

While you work your way up the Mages Guild, I recommend doing the Thieves Guild at the same time. After a while you could start blaming all crime on the Grey Fox (not gonna spoil more than that for you, unless you want me to). As for persuading people illusion's charm spells can be more than adequate. Just stack a few of them (with different names) on whichever NPC you want to influence.

Just a few tidbits:
Frenzy in town is great.

A 100 pt Charm spell on touch is good for bartering, esp if you have the ability to put a 75-100 pt fortify mercantile on self to it. The 100 pts of Charm will also get you out of any bounty/crime less than 500 gold.

Restoration is a great skill, fortify sneak, security for 1 sec, as well as a really evil looking and effective absorb health/magica over time spell.

For an easy target to get initiated into the DB, hit the Morag Tong thug camp just NW of Fanacas, while getting the Ayleid Statue there. I generally recommend the Collect Quest right off as it is the best source of early money. It also has a good darkside path to it as well.

Don't be afraid to get Illusion to 50 asap even as a major skill, also Alchemy, despite what some people say, if you use Alchemy correclty and get it and Illusion to 50 pretty quickly, it doesn't really matter what you do after that. There is a lot of Restore Health, Fly Amanita + Lavender to be had everywhere and lots of poison ingredients.

A decent Illusion and Destruction skill will allow you to cast the combo spell in my signature which is very Nightbladish and you can kill someone in broad daylight in the middle of the Imperial City without getting a bounty, including Guards. Speaking of which, killing guards is a great passtime for a Darksider....