My newest idea for the grand RP community of Skyrim: The Highwayman/Bandit/Marauder

Highwayman
Race: Any
Skill Trees: Archery, Light Armor/Heavy Armor, 1H/2H, Smithing (Optional), Speech (Optional), Sneak, Pickpocket (Optional), Alchemy (Optional)
RP Items: Fur/Leather/Studded Armor, Basic Equipment, Criminal Follower
Stone: Thief, Warrior, Lover, Lord, Serpent, Shadow
Shout: None (The Dovahkiin is no bandit)
Discussion: The theme is about being a travelling criminal who searches for "Random Encounters", Camps, Caravans, and Outposts to rob. Much like the Bandits you encounter in the game, you will never enter any city. This is a very versatile class that can be Heavy and Brutish or Light and Sneaky. Stick to travelling along the roads, hunting for pelts, killing any innocents you encounter, and be sure to get a follower who fits in with the criminal theme.

Thoughts and Comments are welcome

I like the concept, because the Highwaymen in Oblivion always intrigued me.

As far as hunting and gathering goes, if cities are off limits, how would you trade? I'd imagine that you might barter with the Khajiit caravan. Would smaller places like Falkreath or Dragons Bridge also be off limits? Or just major cities, like Whiterun and Solitude?

Also, and I've always wanted to try a character like this, will you just restrict your inventory to what you can carry because you're constantly on the move and live on the land itself? Or will you find a proper place to live?

You would pretty much "take Over" any camps you clear out and live there until you decide to move on again. Trading with Caravans is advised since the Khajiit do not discriminate against criminals. Places that are not heavily-populated or very lawful in themselves are welcome places. Personal restrictions are for the player to decide. You would gather Pelts for leather to improve your gear with, also carrying around a pickaxe makes some since if you need iron for heavy armor and weapons. As i have said it is RP so small adjustments can be made for the individual so that they feel more in-tune with the character

With my personal variant i am going with Imperial (For the Money gain bonus), Sneaky/Archer/Speech Highwayman, and i carry around 1 Stormcloak Cuirass and 1 Studded Imperial Armor so that i can "Sneak" into outposts or camps. I see my character as a sort of Dashing Rogue who's over-confidence causes him to attempt very risky (often stupid) things just to get a little gold, like the aforementioned sneaking into forts dressed as a soldier. He is not above robbing and killing other bandit clans and claiming their camp and loot as his own. I am giving off a piratey vibe arent i?

Oddly enough i am starting to envision him as a Disney Cartoon like Sinbad or El Dorado (If anyone remembers those) or maybe even Jack Sparrow style of comedic villainy

Interesting. I've had a vague impression of this type of character in mind for a few weeks now. Your ideas really fleshed out some of the details. It sounds fun. Plus, if you ever decide that you are dragon-born, you can always just pick up the main quest and go from there.
Thanks!

NP, my ideas are for the entertainment of all

New ideas to add now, if you REALLY want to enter towns, then quietly kill a guard and use their uniform...as long as you dont have an actual bounty it will seem as though you are infiltrating the city. Alternatively if yu want to ensure you dont enter a city go get a small bounty so you are not tempted. Also when you start out do all your trading with Riverwood and then rob em blind in the night. That should help you have a good set of equipment from the start.

Also if you play on the PC (I am on Xbox) you can use the console commands to add yourself to the Bandit "Faction" if you want to belong to a large group

Even more tips, as with Fallout 3 you can get a follower+a dog so be sure to get them as they really even up the fights...assuming you dont accidentally put an arrow in the mutt's skull. For your follower go with a Mercenary as i think all of them are willing to kill and rob stuff for you, but choose one that fights in the opposite manner as you (i.e. Heavy Armor Brute goes with Jenassa) so that you can handle each situation. As my personal restrictions i have chosen not to go beyond steel weaponry. I also dont use any armor that is not made from wildlife (ex: Elven, Glass) and my goal is Scaled or Scaled Horn Armor. My follower is the Merc from Markarth who uses Light Armor but i have him in full Iron anyways (Banded Iron Chest).