I use a fort or escort unit to pre-train my merchants a little on a resource near home. Then I send them off into the world. I usually pick up monopolist a level or three this way. The guild REALLY helps, as does the town hall. Not having the latter significantly increases the chance of the negative "crooked trader" line. That really hurts. When a new trader has that, I tend to just feed it to the competition and recruit a new one.
I don't bother with assassins, though I keep promising myself to try them in a campaign I really role-play. Hungary maybe.
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