Join one of the factions as a soldier. Basically leave your game on auto run till you are max level of soldier and you have a sizeable amount of money. Take leave from being a soldier and act as a merchant to get more money. Repeat 2 and 3 for a while and you will ve rich enough to sustain your own army for a while.
The barrier to entry should be the huge cost, not a perk. It's a bad/mediocre design. You will make more gold with 10 smithing than 1000 trading. Even in the skill description it says level up by running a caravan. Like cmon. That’s for companions. You do not run the caravans, you just sponsor them.
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Here are some things to take note of when buying low and selling high to level up your Trade skill: You need to sell goods that you bought in a settlement for a profit. This means selling

For you people starting a trader or leveling trade. Seriously sell mules, start the game with your 1k, buy some grain and sprint south to the desert and buy as many mules as you can for between 50-100 denars each, after that go to the valdians or nords and sell them each for around 250-400 denars each. Once you start making profits alongside

Yes, I'm pretty sure at exceedingly high levels trade breaks into an infinite loop where you can just repeatedly buy and sell the same item. Pretty sure it requires an absurdly high trade level though, as the trade modifier really doesn't scale that much from leveling trade. (160-something and it's only at like 24% iirc)

Either send them on a caravan and assign as a governor eventually for the three most common Governor skills (trade steward, charm). Or assign your FIRST brother as governor. You can assign his points to begin with. And increase INT, SOC, and End quite a bit (endurance to smith, for free focus points). Then max out Charm, Trade, Steward.
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mount and blade 2 how to level trade