A random character generator that I made that does what it's supposed to do way better than anything else I was able to find on Google. 
No longer will you get Block skill when your character's main weapon is Bow, or no longer will you get College of Winterhold as a faction when your character is a warrior.
With optional Challenges too.

=====About this file===============
As a Skyrim player who entertained the idea of doing a Roguelike playthrough a few times before, I was never able to find a proper random character generator that I geniunely found satisfactory. It was frustrating for me to search for so long and not be able to find a decent one that I liked, which is why I finally snapped and said "that's it, I'm creating one myself then" and spent one weekend to do this. The ideas that I wrote down on the notepad started to pile up as I came up with more features like super rare builds and Challenges. In the end, I've created this for myself in C++, and decided to share it too. 

Keep in mind that this is not exactly a "mod" per se -which is why I classified it as a Utility-, but an .exe file that you run and it will give you a bunch of stats on a black screen about the character that you should build on your next playthrough.
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=====What it does=================
At the first glance, it might all look simple but a considerable amount of thought went into this.

Firstly, it will randomize your character's; 

-race
-appearance (which Preset you can choose on character menu)
-playstyle
-1 or 2 main weapon skills (they will complement each other, you will never get both One Handed and Two Handed at the same time)
-an armor skill
-5 skills (total)
-3 obligatory questlines
-a random optional challenge
-and whether your character is able to use a follower or not and staves or not

But it will randomize these things in a consistent and logical way. How it will do that as examples are:
Chances are you won't get Thieves Guild as an obligatory questline if your character didn't get something like sneak or lockpicking as a skill.
Your character won't get Block if he uses archery or magic as the main way to hurt things.
If your character is a melee oriented character, in order to balance his kit out, he won't be allowed to have werewolf transformation, but there's a chance that he might be allowed to have vampire lord transformation. The vice versa goes for range oriented characters, also classes like battlemages have a chance to be allowed to have either one.
Your character will almost always have a skill to kill things (as contrary to some randomizer out there on the internet). There are a few supporting classes but they are widely rare, and are always allowed followers. 
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======Home rules=================
As this is an utility intended for Roguelike playthroughs, these randomized attributes are intended to be your home rules and restrict your current gameplay of the character.

--If you've got sword as the type of weapon that your character uses, that means you cannot use maces or waraxes dammit.
--Same goes with armor and robes. There is no restriction on rings and necklaces.
--You've got 5 skills in total, that means you can assign perks only to those 5 skills, and you absolutely cannot assign perks to any other skill outside of that list (don't worry, your drawn weapon and armor skills will be in that list too).
--If you don't have Alchemy as a skill, your character isn't allowed to brew potions. Same goes for crafting weapons and armor, improving weapons and armor, enchanting and disenchanting too. (for Smithing and Enchanting skills, respectively)
--You aren't allowed to mine materials unless you have drawn Smithing.
--If your character doesn't have Sneak, Pickpocketing and Lockpicking skills; you can't commit those actions as well. (unless if you absolutely have to do Lockpicking or Pickpocketing in order to advance in an obligatory questline)
--When your character has the Conjuration skill drawn, whether you are only allowed to use Atronachs or Undead is also determined by the program. But you can use Bound Weapons and Soul Trap regardless of whether you've drawn Atronachs or Undead.
--A run can be deemed successfully cleared when you complete all 3 obligatory questlines.
--If you die, you should remove your savefile.
--In the case that you NEED to use a particular tool or magic in order to advance in the questline (destruction spells in Saarthal, or shooting puzzle in Dawnguard DLC), you may use them ONLY in order to advance in said areas and for nothing else.
--The ideal difficulty setting for a run should also be on "Expert" level, not a cakewalk from the start like Adept, and not too impossible like Master and beyond either. This is not a very strict rule, but it has been the best way to experience this kind of playthrough, as I have noticed.
--This one is not much of a strict rule, but if you've got either Knight, Warrior or Berserker playstyles drawn, you should max out the muscular appearance of your character on character creation and make them look beefy. This is definitely not a strict rule and purely serves an aesthetical purpose, it's up to the player.

So embrace your home rules while playing.
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===Optional Challenges=============
Other than the obligatory questlines, there is one randomized optional challenge for each generated character, and you can choose to try to accomplish that if you are feeling ballsy. These challenges vary greatly on the type and the difficulty of it. Sometimes it might be as simplistic as requiring you to kill a specific NPC without getting caught. Sometimes it might require you to buy every house. Or to not use potions. Sometimes it might be as daunting as killing Ebony Warrior or playing on highest difficulty setting. But nevertheless, they vary, and more than that, these challenges are also randomized in accord to your character's other random attributes. If you got the main quest or Dragonborn as a questline, chances are you might get an optional challenge like "don't use shouts". If you are allowed to have a follower, you might receive a challenge like "don't give any items to your follower", if your character is allowed to become a vampire lord, you might receive something like "only travel in daytime" etc.

There is also a 1% chance that your character will receive a Lucky Draw instead of an optional challenge, and this lucky draw will provide an insane advantage to your playthrough instead of a challenge. You can expect something like "you are allowed to Load once", "can choose to put perks in another skill after level 20" and so on.
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=====Other Fun stuff===============
There are a few rare styles in the list of things this program can draw for you, and getting these rare random stuff can be fun on extended replays. I've heard that there are character classes that don't have a main way to hurt others but always have Lucky Draws for example ;)
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==Recommended mods to go with this==
Since this is a utility intended for roguelike playthroughs, the mods that I can recommend simply help further accomplish that standard.

"iNeed - Food Water and Sleep" by isoku

"Frostfall - Hypothermia Camping Survival" by Chesko

"Alternate Start - Live Another Life" by Arthmoor
OR "Skyrim Unbound (Alternate Start)" by chinagreenelvis

"Ordinator - Perks of Skyrim" by Enai Siaion
To spice up your Skyrim skills and perks, it's not really a requirement, but just incase if you are bored of the vanilla stuff.

"Wintersun - Faiths of Skyrim" by Enai Siaion

"Classic Elder Scrolls Attributes" by Ikthelius
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==========Requirements===========
Nothing. Just extract and run the executable.
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===========Installation============
Nothing. Just download, extract the .rar, run the .exe and use it.
Exit and run it again to reroll a character.

Currently, it doesn't have a function to generate a text file of your character, but what you can do is just take a screenshot and save it to remember your character's stuff. I might implement text file generation in the future, but I'm lazy right now.

So yeah, that's about it for now...
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===My similar mods for other games===

Fallout 4 Random Character Generator 
Dishonored 2 Character Randomizer

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