How do you level up your Trading skills efficiently?

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I start by buying iron ore and hardwood in the North pick up some food as well if cheap. Then head towards Aserai lands sell iron ore and hardwood as you move around and buy mules and sumpter horses. Keep buying food as well. Any where you can make some profit do it. As you move towards Empire areas you can probably sell food and horses. Rinse and repeat.
This method only works when you are able to carry lots of goods. Before that hang around Poros and cities close to it buy and sell on trade rumours and slowly build up from there. Sometimes rumours are false but do not worry you will sell the goods somewhere or on rare occasions just sell at a loss.
 
Easiest way I've found to level trading is to amass an inventory size of around 40k and an inventory of about 500 of each basic food, 300 of the exotic foods, 200 of the basic trade goods, 50 of each exotic trade good, and 20 livestock. For horses I limit it to 200 each of the pack animals (but never sell them below my 40k invenory size), 100 each of the basic horse, and 20 each of the war horses. I use the caravan's pick up trade offers perk and keep two caravans running from different towns. Before having the profit tracking perks, I sell red and buy green up to the above listed limits. Once I have the tracking perk, I sell bright green and buy bright green up to the inventory limits above. If I go above those limits, I'll just sell bright green until I'm below my limits. Then I go city to city. If I'm in friendly territory, I'll pick up escort caravan quests. I usually make some good profits at the cities they choose to visit. If I'm in neutral territory of a faction I don't care about relations with, I'll pick up fencing stolen goods quests for cheap extra inventory. If my criminal rating gets too high, I'll take corporal punishment to lower it. I mostly ignore trade suggestions gathered in taverns, they rarely work out for me, but ymmv. Using that method, I'll almost always pick up a point in trade at every city I visit, and at the more profitable ones I'll pick up 3-4 points even at the higer ranks.

This depends on you having a large enough army to keep from getting harassed by bandits, and large enough for all your pack animals to not get slowed down by the herd speed modifier. If you're trying to speed run this, an all cav/archer cav army will have you moving around the map nice, fast, and unharassed.

Edit: Playing 1.4.3 btw.
 
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