Recently, I decided that my main character (who you can see in my profile) needs revising. He cannot hail from Skyrim because of the following reasons:

Khajiit are rare in Skyrim because Khajiit do not like the cold.
His originally planned hometown of Solitude does not befit is view of the civil war in Skyrim, giving him no good reason to side with the Stormcloaks.

Looking at the surrounding regions, Hammerfell seems to be the best option because it is a warm desert region, similar to Elsweyr. I chose the town of Dragonstar because it's close to Skyrim and has a Mage's Guild, giving him access to learn Alteration and Illusion magic.

What I need to know for lore is:
Which side of Dragonstar is more cosmopolitan?
What are the racial relations between Khajiit and Redguards? Khajiit and Orc (because Dragonstar is in/near the Dragontail Mountains)?
Any possible roads from Dragonstar to Markarth in Skyrim?

What I need to figure out is:
The motivation for him to join the Stormcloaks.
The reason he leaves Hammerfell and ends up in Skyrim.

Any help will be appreciated.