Raoul Duke/ Hunter S. Thompson Build

Strength: 3
-He's not super strong.
Perception: 6 (+1 perception four eyes)
-Have to be perceptive to be a journalist.
Endurance: 7
-In real life, HST survived getting stomped by the Hell's Angels.
Charisma: 7
-He's very charismatic and usually solves problems with words rather than violence. If you want to, you can dump charisma to 1 and put one extra point in every other skill
Intelligence: 8
-He's highly intelligent, and he's a Doctor of Journalism y'know.
Agility: 4
-A little below average, he drives everywhere for the most part.
Luck: 5
-Average

Fight the Power - HST was majorly anti-authoritarian
Pack rat - halve the weight of all alcohol allowing you to carry more
Travel Light - He doesn't wear any armor at all, so might as well take it.
Day tripper - do I even need to explain this one?
Toughness - same reason for the high endurance
Gunslinger - Build only utilizes one-handed weapons
Cowboy and/or Grunt - depends what weapon you use more.

Hoarder - He had 600 bars of soap in his car for no apparent reason.
Four Eyes - He wears prescription glasses.

Some kind of revolver, in the movie its called a .357 but it looks closer to the .44 in-game, in the book it's described as a snub-nosed revolver, similar to the police revolver from Dead Money, so really it's dealer's choice.

.45 pistol or 'A light shining in darkness' from Honest Hearts. HST killed himself with a .45, and a Light Shining in Darkness fits because he quoted the bible a lot.

You can use this mod[www.nexusmods.com] for a more accurate outfit, plus some extra stat boosts, highly recommend.

For vanilla New Vegas, use the pre-war Spring/Parkstroller outfit[fallout.fandom.com]; and for the rest of his outfit, use the trooper helmet[fallout.fandom.com] and the Lucky Shades.[fallout.fandom.com]

Caesar's Legion
-You need to be at least accepted to get the Lucky Shades, but he would not side with them.
NCR
-He wouldn't side with the NCR due to his anti-authoritarian ideals
Mr. House/Independent
-Either Mr. House works as a stand-in for the magazine he's writing for, or Independent Vegas again due to anti-authoritarianism.

Great Khans
-HST spent over a year living among the Hell's Angels, so it stands to reason he would be chill with the Khans.
Brotherhood of Steel
-He would wipe out the Brotherhood of Steel by blowing up their bunker.
Boomers
-He would admire their high firepower and self-sufficiency, and would ally with them at Hoover Dam.

Raul AKA Dr. Gonzo AKA Ghoulified Oscar Zeta Acosta

The only real "rule" is to carry as much alcohol and chems as you can get your hands on and use them as much as possible.

Try to use speech and barter to avoid conflict as much as you can.