For the gear I was trying to do a simple hat-armor-gloves-shoes spread but Ning wasn't having any of that with individual pics, so I tried my hand with MSpaint and it was being difficult as well.  Ended up going with just the armor to save a huge headache.

The new perk spread alone was enough to clean up the build but I came across a few really good pics in the process (the tangled one being one of my favorites).

Thanks for your valuable input.

But that's wrong, you can't be AS viable with 8 perks in combat skills compared to 8 perks in Alchemy and Enchanting.  Not to mention how much longer it would take to train or level those combat skills to 60 as opposed to leveling crafting skills to 40.  You don't even have to grind at all, just naturally progress while you are in thief mode.  Admittedly it can make you way OP if you have no self-control, but it can also be the quickest way to achieve your desired archetype if done with balance in mind.  That's precisely why I have went to such lengths to provide exact step by step instruction on how to become a duelist without becoming OP.  I don't think you are qualified to comment on my methods until you test them for yourself.  I will tell you this though, by level 30 I guarantee you can't have a duelist that is anything other than a generic warrior whereas my duelist has a silver tongue and tons of connections across skyrim. Also it can get boring to spend 40 hours playing the same combat style with nothing to change the pace.  That's why I'm so happy with how this build turned out, because by the time you are bored of being a thief you are ready to become a bad ass duelist.

Time to give you the critique you requested.

It's a solid build and it does offer some nice RP'ing perspective (although I can only imagine how odd it must be to have Delvin talk to you like a stranger at first :P), but I'm not entirely sure I like the switch from the crafty thief to the honorable duelist. I'm not sure if I missed this, but I don't entirely see a proper reason to do this massive personality switch. Wouldn't it be more logical to focus on your career as a thief instead of traveling the lands as a warrior? o.O

To be honest I don't particularly like that you have to use glitches or exploits to gain powerful enchanted equipment. I understand that this was your attempt at differentiating your character from the rest, but to me it feels like a grind to get to level 25 and really start your build. Maybe there's a way to just drop Alchemy and put those perks in Enchanting and give a more natural enchantment as you level it?
One thing I also wonder is whether the duelist will still resolve to thievery. It'd seem a bit odd to me that Pickpocket is a main skill if you only use it for the first 25 levels. Otherwise I don't see the point of perking it. o.O

As for the combat tactics as the duelist; they certainly are original. But they do seem a bit clumsy, especially the Drunken Stance. To me it feels a duelist would be all about speed and grace and focus more on your Acrobat skill which I feel fits the mood of a duelist. 

Overall I think this is a solid build to work with, but I get the feeling your desire to differentiate this build from the rest doesn't work in your favor. I see why you try to add things like a combination of clothes and light armor or your special moods, but I don't feel they're necessary. It's a nice build all on its own and to me it's mostly the roleplaying that'll seperate it from the rest. And you really don't need the enchanting/alchemy loops. Just focus on either skill and you'll be powerful as it is.

Back in D&D a rogue could develop in to a prestige class called  a duelist.  A rogue is basically a thief.  The personality switch is justified by helping Glover and Sapphire.  By the time you are level 25 you will have well over 50 thousand gold if you are half the thief you should be.  No need to steal after that.  You can still use sneak and poison planting for tougher groups of enemies, so pickpocket still has it's uses.  My exploit is tailored specifically to keep from having to grind the same old skills to become viable in light armor and one handed and especially to make one handed sword blocking as viable as I wanted to see it be.

With 8 perks, 4 each in Alchemy and Enchanting, you can essentially make your desired archetype at level 9!  It's easy to make yourself OP, but it beats the shit out of playing for 50 hours before you start to see your build take shape.

Thanks for your critique, you would be really surprised how fast you get to level 25 when playing a pure thief.  It's an alternate means to a slightly different end than most warrior builds. 

Really like this build and will definitely try it out! +1 

I'm not a stranger to thief builds as they are my favourite. Hell, my most enjoyable build so far has been a full thief build. The thing that keeps a thief build fresh is strategy. If you go in slitting throats all the time it'll get a drag before too long. I feel this build lacks proper strategies: it has a few special attacks, sure, but beyond that it does feel like the average thief. And as this build is family of Delvin I fear that won't do. 

One of the things you could do, especially with your duelist transition, is to try and create some synergy. Poisoner could be useful, but I'm more thinking of an honorable duelist who DOESN'T play fair. I can understand that you took inspiration from D&D, but even then the transition from thief to duelist is too sudden. It would make more sense for me if this build becomes a combination of both a thief and the added warrior skills. Sneak, steal weapons and poison your own blades and THEN start going into combat mode and defeat your opponents. It would still fit with Sapphire having inspired you, as you could still be doing the right thing.
The way I would roleplay this build (and use your skills) is to play as Jack Sparrow from Pirates of the Carribean. He's dishonest and lies (speech), he sneaks about trying to accomplish his plans (stealth and pickpocket) and he's no stranger to sword fights (one-handed and light armor). But at the end of the day he will do the right thing, especially if it could yield him some profit. It would make more sense to me than a deus ex machina change of heart.

As for the alchemy and enchanting glitch: even if you can easily get to lvl 25 to turn into a duelist training both skills will still be a grind. I don't question the easy way to level up stealth skills, but I also know that the craft skills are very slow. Money would speed it up, sure, but even then it takes quite a bit of time to get them to high enough levels that your exploits become worth it. I don't really see how you would have a problem grinding One-handed and light armor (the former which levels naturally and the latter which could easily be trained with trainers) if you have no problem grinding alchemy and enchanting.

I'd like to change my opinion and say that you should go with alchemy (Thieves Guild armor and Nightingale armor should be sufficient) and focus more on gameplay rather than exploits. I also don't really see the point of roleplaying a character if you aren't interested in investing time to create and mold it to your liking. Being overpowered simply takes away any challenge for me and that's one of the reasons I tend to play as thieves. Thieves HAVE to rely on strategy in order to survive, so in essence I feel that you are trying to create a character that doesn't have a thief feel to it. I'd say that's important if you're trying to get your duelist, no?

nice build man. I will prob try it out at some point :)

Wow this is a really long build. But it is nice! You have my vote to survive the Deathmatch.

Wow, 15 likes already!  Only 15 more to go! 

Love it! The concept and the gameplay are fantastic. This type of character is by far my favorite.