My first character had high Charisma, Luck and Intelligence, tagged skills Speech, Lockpick, and Survival (in hindsight, a bit of waste as Hardcore mode wasn't as hardcore as I'd hoped), who was a failed writer-turned-desperate alcoholic whose best moments would come when he was drunk, hence the need to take on crappy, dangerous jobs like that of a courier. A good 25 or so pounds, minimum, was set aside for alcoholic beverages in his inventory.
Ah, Cass and I had some great times

We never trusted House for a second, NCR were too incompetent with their bureaucracy, Legion were arseholes, and so Yes Man was perfect. Bloody shame though that we ended up killing so many innocents at the 188 Trading Post and Sloan when NCR turned hostile (no, not Snuffles, too!), and I definitely didn't like it when the Remnants mistook us for the enemy at the Dam
2nd playthrough as a homicidal, beautiful, dumb blonde with high explosives was great fun, and being the first woman honoured by Caesar was a great ending.