Trailer park boys Skyrim Builds
Race: Imperial (For Speechcraft + Coin Bonus) or Breton (dragonskin perk)
Faction: Thieves Guild + Bards College
Perks: Alchemy (For Skooma making) + Speechcraft + Pickpocket + Destruction + Light Armor*
Also: Ricky has been shown to take insanely high levels of shit. He needs to have items that let him resist shock, fire, and frost. Health levelling is perfect. Light armor would be my choice, but heavy armor could work if you want to. In terms of Speechcraft, prefer intimidation/bribe. You should have a horse, but don’t worry about it dying. It’s gotta be the equivalent of the shitmobile. Shoot first, ask questions later.
Race: Imperial (Speechcraft + Voice of the Emperor)
Faction: Thieves Guild + Bard’s College
Perks: Speechcraft + Pickpocket + Heavy Armor (for unarmed bonus) + Destruction + Archery
Also: Julian is almost always drinking, so save some of your inventory for any type of alcohol. Focus on stamina and health levelling. Prefer persuasion+intimidation whenever possible. Being the thane of most of the holds should help with your crime bounties.
Race: Imperial (Speechcraft) or Khajiit (cmon b'ys y'know why)
Faction: Thieves Guild (optional but hey why break the pattern) + Bards College + College of Winterhold (Smartest of the group + to train Conjuration)
Perks: Conjuration (gotta have them kitties to help him fight) + Speechcraft (merchant perk) + Smithing (From his cart repairing and general handyman skills) + Illusion + Sneak
Also: Steal from shopkeepers and then sell their shit back to them. Use the animal allegiance shout to get your sabre kitties to follow you. Avoid confrontation as much as possible, Bubbles isn’t the type to run headfirst into a fight. Prefer Persuasion+Bribe. Be the voice of reason. If you do the main quest, try to be neutral and do seasons unending. You can do the companions if you want Eorlund for smithing training.
If anyone has any other suggestions, give a shout!