Just want to start by thanking each and every person who replied to this topic. The replies have been educational, and inspiring for what I want to do in equal measure. I'll pick out a few items to respond to as they appeared in the thread ...
Stealth and Thievery: Yeah, they fit the character alright, and I've never played a game focusing on either skill so that fits in with my wish to play differently, so I'll probably give them a go.
Marrying Trader's sister: That's fantastic!

I love that someone figured out a way to kill him. I may keep this in mind and carry it out just as a nod of respect to this thread at some time in the future.
@Valadir : That was great. I know what you mean about killing for a reason, and that's sorta the way I intend to play going forward. I'm going to try and use the characters around me to aid my rise to power but if someone crosses me and I don't see a use for them, I'll look to backstab them repeatedly until they fall down

Dark Brotherhood: Having steered clear of spoilers thus far, I don't know a lot about this guild but they do sound to be the type of guys I'll want to hang around with. I think I've heard you get backstabbing bonus from being a member? That would be cool.
@Leold: Love the avatar, and coincidentally my evil character is named Biggus dikeus!
'Neutral Evil': yeah that sounds like the way I want to try playing going forward
Classes/Skills : Not sure how I definitely want to play yet, but the advice here has been very helpful towards making that choice in the coming days/weeks.
No Murdering of Kids: That's way worse than a bummer. Thank god there's a mod for this! Must go grab that asap. Kids can be the most annoying things on the planet and in-game kids are even worse, so I need to be able to wipe them out or I might turn on myself!
Avoid the main quest: This may prove to be invaluable advice for this playthough as it seems like quests of interest to me would be unavailable if I progress on the main quest, is that right?
Vampire: That sounds class! But as above would that close any significant doors for me? It wouldn't restrict me to 'nighttime' movement only would it? I do want to explore the dark side of the game but not necessary if it means I miss out on significant parts of it.
@roosterdad: I know what you're saying but I'm just looking for a change of pace. Being virtuous is likely more natural to me alright but I've done that in a number of rpgs in the past. I could have tried to go evil on my own, but I didn't want to waste hours coming to terms with the new strategies that aren't 'natural' to me, so I've just looked for some pointers to help me get immersed quicker and I think I've gotten them. Not trying to be the best (worst?) evil character ever, but just get down with my dark side for a change
@Everyone: Honestly, this is far more advice and help than I ever expected. You are all a credit to this community and the fact that you all probably think nothing of taking the time to help out in this and so many other threads is testament to how strong this community is. I'll check back on this thread just in case there are further replies, but I definitely have enough to stop talking and start playing for a while. Thanks again, but as I now leave to get in character, may the fleas of a thousand camels rest in all your armpits, and if you ever come across me in Skyrim, I wouldn't turn my back if I were you
