I'm creating yet ANOTHER character, and I am planning on having him move to his ancestral home: Solstheim. His backstory is that his family lived in Solstheim even before it was given to Morrowwind, and when Red Mountain erupted, his family moved to the Imperial City because they thought it would be safe. They were dirt poor for 200 years until the Great War, when they lost what little they had. Literally everything they owned was destroyed. The small farm they lived in outside of the city was taken over by the Elves as a headquarters for officers, and they were displaced. Until the start of Skyrim, his family had to either live on they destroyed farm (trying in vain to fix it, although some crops still surprisingly grew, giving them at least a little income) or in the slums inside the city trying to earn money with the Thieves' Guild. My character (who I have yet to name) has decided to return to Solstheim to earn enough money to pay for his family to move back home. He has decided that Skyrim's Civil War and the eruption of Red Mountain will make for lots of potential for being a wealthy merchant (just like what the Khajiit caravans tell you). While he is on his way to Windhelm to take a ship to Raven Rock, his convoy is attacked and he his captured because he was near a group of Stormcloaks who were taking the same road. He was brought to Helgen and was about to be executed when a dragon attacked, etc. etc. etc. The problem is that he lost the money he was carrying with him to pay for passage to Solstheim. It will take a long while to earn enough money for another voyage, and it will take even more money to pay for housing and such, seeing as there is not much work on Solstheim. We know he will eventually become a rich merchant (or will he?) but my point now is this: should he start his merchant trade in Skyrim until he can earn enough money to go to Solstheim, or should he just join the Thieves Guild? The problem with the Thieves Guild is that they wouldn't want him to leave, and him being in Solstheim away from the Guild's fences would mean he is not being watched, and him not being watched means he could snitch, and thieves don't like that... Anyways, tell me which job you think he should take on, and tell me what you think of my character and any good names he should have, thanks!

He could start a career making and selling potions. First collecting ingredients in Skyrim and then when he has enough for passage he could journey to Solstheim to collect the unique ingredients there. Alchemist is a career you can literally start with nothing since collecting ingredients is free. And as a career, it eventually becomes one of the highest paid things you can do. Since Solstheim has ingredients that cannot be found elsewhere it adds another reason for him to journey there. You could eventually add assassin for hire to a career as an Alchemist as well, since the 2 go together. Dunmer are natural Alchemists and assassins as they get +5 to Alchemy and Sneak.

If he eventually lives on Solstheim at Raven Rock or Tel Mithryn he will also have access to an Alchemy table.

That doesn't seem like a very sustainable career... Pick flowers in Skyrim, go to Solstheim, make potions, sell them, then what?

I'm probably going to become a pickpocket

Pillage, [censored] and plunder.

You could always join the TG then rp that Delvin asked you to check up on his brother, you could then after doing a few odd jobs for the locals to get yourself known and split your time working in the mines and selling your merchandise (whatever you chose your main profession to be) to the other traders around the island. For example, make a few items in Raven Rock and sell them at Skaal Village and vice versa.

Prostitution.

Kidnap children and force them to work on your mines!! And sell drugs and kill guards for random reasons.