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Having an extra one is just overkill
Also taking more than what the game usually lets you takes away the weight of some of the story developments
Since keeping gear up to date is already an expensive thing, you might want to consider having at least two thievery characters to snatch the money and gear you'll need. Always steal gear first, money second. Its more efficient to steal everything else and top off on cash than it is going straight to stealing gold, unless there is nothing you want or need.
(Aside: Am I the only person who never steals anything? I've finished the game twice, once on honor mode, and I think the only thing I've ever stolen was a hat in Fort Joy to get the achievement...).
Love pickpocketing; I'm so glad they added it; it takes some skill to steal from certain NPCs and to be aware of sneak cones. It's a skill in itself TBH.
OP, rather than starting with an extra character, I'd recommend playing four characters in Story Mode, the easiest difficulty. Working out a good build and gearing 5 chars will become very challenging, and might be a bit of a headache.
GL