Developer API is a great idea IMO, especially since a lot seem to be willing to contribute to the mod in various ways.
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Here's how a Caravan goes. Maybe it's easier for people with many fiefs /w multiple owners producing.
Remind you that I'm not just talking about sending one guy from point A to B, e.g. you produce goods, go somewhere and sell. I'm talking about actual trading, where you swap goods with someone across the map.
1: Talk to factions to setup trade.
2: Find 1/2 characters to send out
3: Figure out how many troops is needed to carry the specific crates on the caravans
4: Transfer each set of items manually to gear up the caravan
5: Check with everyone if they have the right speed, weight, etc to make sure you haven't transferred too much
6: Tell your guys where they need to go and what to do
7: Teach people how trading works since most never did it
8: Make sure people connect and do the trade, usually hard since everyone is on at very different hours
9: Repeat all the time since people have to dump their troops at least (for less upkeep) into the town, usually dumps gear too.
