Ok, so this post is as much for myself as anyone else. This is really a place for me to write up the backstory and ideas around the Skyrim characters I'm currently leveling, but if it gives anyone reading it some ideas for their own playthroughs then that's awesome too!
Scout Draccus -
Draccus is a scout with the Imperial Army. Dropped in Skyrim behind enemy lines during the civil war to scout out Stormcloak positions. Unfortunately during this he was caught along with many Stormcloak soldiers by a group of Imperials. Having not yet been made known to General Tullius and having no papers of identity or uniform on him, to avoid being spotted by the Stormcloak soldiers, he was to be executed along with them when a dragon attacked Helgen. After escaping he makes his way to Solitude to once again join the Legion. Many would question this action after they nearly killed him but he's loyal to the Empire and understands if he'd kept his papers it wouldn't have happened. After helping the Legion crush the Stormcloak rebellion he retires as a soldier to stay in Skyrim. Later joining the Companions of Whiterun, and then the Dawnguard as the vampire attacks become a problem. Now he travels Skyrim and Solstheim protecting people across the land, with the honour of a soldier.
He will not join the Thieves guild, as he sees stealing as honourless, nor will he join the Dark Brotherhood as he only kills those who threaten others. The Mages' College is of no use to him either.
Sneak - one handed (dual wield) - archery - light armour - smithing
Storm-Caller Drakir -
Drakir is a Nord, one of an ancient bloodline. He has traveled Tamriel for years searching for others like himself. He is a Shaman, one of the last. The Nord's recent distrust of magic has made it hard for him to find anyone to pass on his unique brand of Nord Shaman knowledge onto, and thus he may end up as the last of the Storm-Callers. He has no affiliation in the civil war, having been nearly executed by the Imperials when he was picked up with a group of Stormcloaks who had shared their camp with him on his arrival back in Skyrim you would think he'd side with the Stormcloaks, however while he understands the cause, being as well traveled as he is he doesn't agree with Ulfric's rejection of other races, and also feels the Empire may be the best way to keep the Thalmor at bay (seeing as they vehemently hate the Shaman way of life and use of magic) as well as keeping travelling routes open for all.
As his name suggests the Storm-Caller uses the power of the storm in combat, utilising frost and shock magic, alongside Frost and Storm Atronachs and his two axes, usually also enchanted with frost and shock effects. Slowing and weakening foes with hits from magic before sweeping in with fast, sharp attacks from his axes while the elemental atronachs aid him.
The Mages College is a definite place to go for the Shaman to enhance his knowledge. His protective nature will also lead him to defeat the great evils of the world, Alduin, Harkon and Miraak to name a few. The dark brotherhood, companions and thieves guild are paths this protector will not take. The civil war may be done either way if he makes up his mind but he is no soldier.
Light Armour - Destruction - Conjuration - One handed - smithing - enchanting
Lord Drakkul -
Lord Drakkul is a Breton of renown within the Empire. Rising through the ranks in the Legion and with some impressive feats on the battlefield he became a knight of the Empire. However after some time he became bored with the politics that comes with this and abandoned his country mansion in search of more power. The power that many mages wield, the power over the mind and the power over life and reanimation had always intrigued him. Shedding his wealth and title so as to not arouse suspicion as to his identity, afterall how many necromancers would trust a knight of the empire, he went in search of the more villainous mages, the sort he would normally rescue villages from, in hopes of gaining their knowledge. Now he has ended up in Skyrim. His money and identity back in his Daggerfall country mansion, he wishes to try these new found powers on all who stand in his way.
With the aim of becoming powerful and famous within Skyrim itself he will strike down any who try to stop him. While he must keep his necromantic practices secret from the general populus, rumours will be spread about him.
A behemoth in plated armour with a massive axe, he can barrel in swinging through any enemies, but also likes to mix things up with illusion, causing his foes to fight each other for him, and necromancy. The fear and confusion on the faces of his enemies as they kill each other, and then get raised from the dead to fight their friends again fascinates him.
Do not mistake him as being intrinsically evil however, he will still fight evil, Alduin, Harkon and Miraak being the obvious ones. His obsession with manipulating his enemies minds and life force does not come from cruelty and he will not do it to those who would not hurt others. However he does do things for personal gain more than to help others.
Dark Brotherhood and Companions would be good places for Lord Drakkul to start and he may well return to his roots as a soldier to fight in the civil war. He would benefit from joining the mages' college also, as it's a place he can practice his necromancy without the judgement of others. The thieves guild would not fit this heavily armoured tank.
Heavy Armour - Two Handed - Conjuration - Illusion - Smithing - Enchanting
Knight-Paladin Dracsus -
Dracsus was originally a knight who discovered he had a gift with healing magic, however he found the edicts of the traditional Paladin orders did not suit him. No drinking, no marriage, all politics and no action. Plus the Paladins had a very black and white way of looking at the world, you're either evil or you're not, whereas Dracsus' experiences told him that nothing was that simple, people could do evil but with noble intentions, or vice verca. As such he named himself Knight-Paladin. A knight with the capabilities of a paladin but without the restrictions of their various holy orders. He seeks to destroy sources of pure evil but help those who have no choice but to be evil. This can sometimes lead to him being taken advantage of however, which is how he has arrived in Skyrim with nothing but rags.
He will never claim to be flawless nor expect anyone else to be.
Mages college presents him with opportunity to expand upon his knowledge of restoration magic and the civil war could use his hand. The thieves guild and dark brotherhood are too questionable for his presence however. He is not, nor will ever be a sell sword and thus companions would not be a good fit. The dawnguard however would be an obvious home.
Heavy armour - one handed - restoration - smithing - enchanting
Pirate-Captain Dracholos
Dracholos started out as a captain in the Imperial Navy, however due to some misjudgements of his higher ups, for which he got the blame, he sailed the seas as a pirate for many years. While still loyal to the empire he made sure to only attack merchant or Thalmor ships, he made an exception when he spotted the ship of the admiral whose decision had cost him his career. While getting his revenge he lost many of his crew and was left with barely enough men to steer the ship to ground. Skyrim was the land on which he grounded, on the northern coast. Here he and his men went their separate ways, each in search of their own fortune. With his trusted saber in hand he will ravage the land as he did the seas in search of fortune and fame. A silver tongue and some magic tricks insuring all around him will listen and fear....
Any quest line really is open to this guy due to his flexibility and mix of skills.
Light Armour - One handed - Illsuion - Smithing - Enchanting - Alchemy - Speech - Maybe sneak.