Thank you Nox for taking time and answering.
@2 Yes. Maybe the "ask for work" option should be eliminated of it might be a more... delicate way to treat a lord/kind yes? Replace it with "I understand you wanted to ask for a favor, major?", then the major can give the player a job, but one worthy of his prestige: wiping out some bandit nest or rescuing a damsel in distress, not some cheese delivery in other side of the country.
#3 Same thing for nobles.
Economy. You pay for a soldier like 10 gold (ermm... thalers) but for a bag with 30 arrows you pay 300? For 14 bullets 1000? For some fluffy hat 200? For a pig you pay 10? For 2 baskets of apple you pay the same as you pay a man ready to die for you? Something is wrong, soldiers should be way more expensive.
Caravans. Thery are GREAT. But... if invest money in one, why can't I spend more money for more guards and send it on its own in target city? Why I have to escort it? I don't want that. I'm busy with other things. Other caravan. Or maybe 10 other caravans. Or 50. And when it reaches the target city, why I must sell the goods there, even I don't like the profit I make? Why I can't send it in other town?
Might. Ok, I have towns, and villages and armies. I was like a hurricane over the Eastern Europe and I slaughered countless men and women (btw, where are the kids? how the villagers breed, by cellular division?) and now no-one dare to oppose me. Really? How about nature? Floods, droughts, locusts>
Those will mess your propersties for good, and not let you become overconfident. As for your troops... there are diseases. We are talking about middle age here, right? People are supposed to die from poor hygene and bad healtcare more than from arrows and bullets and swords.