I'd love an autonomous port town / pirate haven. Nothing big enough to be a city state. More like a ramshackle village too remote and too dangerous to govern, where pirates, mercenaries, smugglers, courageous merchants, and enterprising rogues are guaranteed passport, since there's no solidified political affiliation. Think Riften, but without the pretense of official governance.
Region / Geography
- It would have to be along the northern coast as that's where the water is. North east is too frigid and the land is all icebergs. Northwest is too close to Solitude and Imperial attention. Perhaps the entire place is built in the yawning mouth of a huge cave so its easy to hide / defend.
Architecture
- Ramshackle, but cunning. The kind of useful chaos birthed when roguish ingenuity cavorts with pseudo-anarchistic freedom, but constrained by available materials & labor. Lots of shacks and lean-to's crammed together and some Jorvaskrr style longhouses fashioned from reclaimed boats.
- The fanciest buildings would be functional and adorned (like Jorvaskrr), but not grandiose, like Dragonsreach.
- Everything would be centered around the docks, with very little sprawl beyond that (especially if the port is inside of a giant cave).
Townsfolk
- Being a haven for outcasts and adventurers, there would be much more diversity. Nords would be drawn there by proximity alone, especially the criminal, outcast, and lawless. Redguards of nautical / piratical bent would naturally be drawn there. Khajit merchants would be a no-brainer too as the place is one giant black market. They would, ostensibly, bring along whatever mercenary muscle they needed as well. Imperial's with outcast political affiliations, or spies of the Empire seeking for trade in information. Perhaps some Bretons seeking adventurous mercenaries or black market magical artifacts. Orcs looking to win glory outside their holds seeking employment as pirate marines or sell swords. Basically the dregs of Tamriel, brave, dangerous, and unlucky.
- For giggles, perhaps there'd be a couple poor besotted missionaries from The Imperial Cult or The Temple, trying to "help" the wayward.
- Every merchant would be a fence, regardless of your thieves guild affiliation or speechcraft perks.
- Black soul gems, skooma, rare & heretical writings, and moon sugar would be readily available for those with the coin.
- There would be tons of follower enabled NPC's. Tons. (and it would be a great opportunity to get any race/gender/class combo you wanted, rather than Skyrim's already limited selection)
Leadership
- The port is in Skyrim territory, but there's no official jurisdiction, so there's no Jarl pressing claim. Indeed even if there were, that Jarl would be hard pressed to actually enforce the claim given the powerful entities that call it home (mercenary groups, pirate bands, reavers, and merchant princes).
- The actual leadership of the town would be composed of a small, ever shifting, council of the strongest interests, likely dictated by who's got the right combination of muscle, money, and connections. The politics would be cut throat, with blackmail, bribery, and assassination being commonplace. Leadership of the council would naturally fall on the most dominant personality... however long he or she lasted.