How do you make enough money ?

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Tournaments combined with running trade routes is very lucrative till you start investing. Build up a decent warchest before you take your first castle or town. Just keep asking the tournament master in each town where the next tourney is and keep doin that while doing maximum bets.  Also a good strategy , well at least works for me is bribing other kingdoms to make peace. Took a town from Swadia, first noble I met I paid off 20k and all was well :p Gives you enough time to build up a homegrown garrison in case they attack again, but obviously they won't for a whole month. 
If you have decent Leadership making money of prisoners is easy too just get yourself a blunt lance and attack party s that have slaver prisoners so you can recruit them.
Atm I'm playing as Knight with only one castle so money is always an issue since my upkeep is like 10x my income but after you go through 2 100ish Sea raider/Bandit party's  moneys not that much of a problem 60 prisoners make like 6-8k plus loot for like 2-4k.
Some good answers. Now here's some more.

Attack the Black Army. They drop tons of two handed swords that "sell" for over 300 denars each.  You can make an easy 40k for every black army attacked.

Disband all Calradrian and mercenary troops.  Use only troops from the refugee countries. No matter which faction you are playing you can use the other refugee faction troops if you capture them and recruit them.

Garrison your troops and travel around with as few as possible.  When I'm using horses for myself and my companions we all have Heavy Chargers and the 11 of us can take on 200 Sea Raiders as we get higher in level.  The loot is sick but you also gain a lot of renown. 

When I want more cavalry in my army I use only one cavalry type--Zerrikanian Reapers!  They all have blunt weapons and cost a fraction of what Slavers cost.  Plus the Slave Masters often don't spawn with a weapon they can use on a horse.  Zerrikanians will make you rich with prisoners.

Before a big battle create a regiment of one soldier and make sure that soldier enters the battle with you.  This little regiment will soak up all the prisoners you capture as well as any freed prisoners in the armies you are attacking.  This can give you an emergency boost of troops if you are forced to rest due to exhaustion.  Now guide the regiment back to a city and start selling the troops.  When the invasion comes you will make hundreds of thousands of Denars doing this.  And if your city doesn't have a Ransom Broker inside you can store the whole regiment in the city and pull it out later when a Ransom Broker shows up.  You will still need high prisoner levels or else transferring prisoners from a regiment to yourself to the Ransom Broker will take forever.

You an recruit captured mercenary officers into your army. Black Army, Serpent, Warbong, Conquistadors all have officers who will become part of your party.  Once in your party you can level these much higher level troops in the training skill and give your other companions a boost. Also you can strip them of equipment and release them.  Even if they are in your army another officer will spawn with a new Black Army (for example).  So there will be two Morgar Blasius' in the world. Strip your Morgar of equipment before fighting the newly spawned Black Army and release him and then you can capture him again with all new equipment.

If you are using Reapers and have armed your companions with blunt weapons (I prefer Balanced Flanged Maces--best weapon in the game IMHO), then you can put an entire Black Army in a regiment and tell that regiment to wait near Sea Raiders or Steppe Bandits and let them capture the whole army of prisoners. Now attack that army again and you will have all the loot that dropped before.  Sometimes the Black Army drops so much expensive loot that you have to go to several cities to sell it all.  It's that valuable.

I've had mixed results with the trade investments. I've never really made any money off it.  In fact, when I had almost all the cities in the game as well as a bunch of guilds I was still losing money on trade.  I owned all the cities but does it matter if I control the city or can my lords control the city and I still get the benefit of the guild?
One more thing, if you are thinking about taking a castle you should try to capture as many refugee country troops as possible and recruit them into your army.  Just keep them as prisoners in a regiment and stash that regiment some place where it won't be attacked by anything.  When you get a couple hundred start recruiting them.  This way you won't have to pay for them until you need them and once you have them they won't cost you a fortune to keep throughout the game.

Also, forest bandits make pretty good castle assaulters because their arrows kill pretty well. And even though they are more likely to die at the beginning of a battle (I put them at the top of the list so they spawn first) they will likely drop arrows for you to shoot at the defenders.  This is a huge advantage and they only cost you 5 denars a week to support.

Finally, you only need to put a few men in each castle.  You can take all the rest and keep taking castles until you run out of men or castles to take.  Why do this?  For starters castles are strong points that can hold off attackers for a while.  When they are under seige you just bring in a larger force from somewhere else and run the attackers off. So long as your don't go too far away from your castles and have a mobile force to pour into the castle to help defend it you can have a lot of castles but just a few men.

There is an old Holy Roman Empire (Germany) saying that expresses this strategy, "He who defends everything defends nothing."

Right now I've got 3 castles and one city (Yalen) and I don't have more than 300 men TOTAL.  I am about to conolidate what I've got and attack Jelkala since it's been weakened by the Kergits and Swadians.

I will put a permanent garrison of 10 men in Jelkala and use the rest as a reactionary force to defend my realm.  I may even take Veluka as well.

Someone asked how you take cities with just a few hundred men?  First you need lots of archers. Probably two thirds of your army or more depending on if they have good combat skills.  Put them all at the top of the que and let them kill the defenders on the wall.  Keep any infantry that spawn up close to the wall where they won't be under fire.  Sometimes if you put them just to the left of the ladder the defenders turn towards them and expose their unshielded side to your archers.

When all the archers have run out of arrows and you have fired all of yours, then send them in to attack the castle.  If you have high surgery most will just be knocked unconscious.  When your reinforcements arrive recall all your archers and let the new archers loose all their arrows as well. I don't remember how many reinforcements you get but I think it is three.  When you run out of archers send in the infantry.  Their weakest troops should spawn last and it will be an easy battle.

Remember, that it doesn't matter if the have 10,000 men in that city.  They are only going to be able to bring a few hundred to bare against your army.  Then there will be a second and third battle.  If you can win those then you capture all the remaining troops!  So make sure you deploy a regiment before you assault the castle so you can soak up all those prisoners.  To do this, just wait until the ladder or tower is built and then when the game says you are ready to attack go to Party and talk to one of your troops and tell them to become a party.  Then briefly continue the siege and then click on the game to bring up the attack options again.  You will notice that the regiment has joined the battle. Now you KNOW you will capture troops.  If you do it too soon then your regiment may be run off by enemies or bandits or it may engage in battle and wont' be able to assist with the castle battle.

Best troops for attacking castles are Villianese religious troops. They come with great armor, weapons, and powerful bows. Put them at the top of your cue and you won't even need infantry.
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