The way leveling trade in this game works is so bad, its so so so freaking bad, trying to level up trade will bore anyone to tears and i hope the devs just make operating trade caravans give xp, because otherwise its a horrible chore. A dozen trades are enough to reach 300 Trade, but you need a lot of resources for blacksmithing.
Edit: For leveling companions, set up controlled encounters. For example, say you want your companions to level bow. Find some forest bandits and make a shield wall. Place your companions slightly behind and offset. Then the shield wall will soak up the bandits' arrows while your companions gain XP. Desert bandit hideouts work best for this.
I'd try to get up the skills that are hardest to get in gameplay. Mainly leadership, since it takes FOREVER to level that up even a little bit. Tactics and medicine are also on the list, though they can level a bit quicker once you put all your points into them. Weapon skills are easy to level in gameplay, so I'd avoid them.
Get a few workshops and get the perk for trade rumors from your workshops. Then just go off that. That's the best way I've found so far. This comment was from 8 months ago, they've since updated it so trading horses and mules isn't great. Best way I've seen to level up trading now is the caravan exploit.
RE9afm.