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Talk to the mayor, and ask about sending caravans.
Azazel makes some good points, but I'd honestly say that he's missing more than a couple ways, including several that I think will fit your style more.
First and foremost, you say that your usual routine involves arena training for money and experience. The good news for you is that there's still a mechanic very much like that; go to the taverns and find someone named "Pub Visitor" and challenge him to a (consentual) fight using the "My fists are itching" choice, then choose the amount of money you'll be wagering for, and then beat the living tar out of him. If he refuses, you might have to get him a bit more drunk by proposing a toast to the faction ruler of the place you are in.
You can actually beat him up quite a lot of times per man and get a decent amount of money for the early game plus welcome boosts to your proficiencies, but eventually you're going to exhaust one individual guy. In that case, just go to the next town over's tavern and repeat the process as much as you want. Just don't do any of the other options in the dialogue because they'll force you to fight to the death and will tank your reputation in the place you're doing it.
Then there are always the "Milk Run" missions. That's my name for the quests from the various Village/Town/City/Fortress/Lordly notables that don't actually involve combat, like delivering a letter from Person A to Person B. Those are surefire ways to build your capital peacefully and also to help raise your stats with the various locales and lords.
Between the two of those, they're probably how you're going to get your starting capital.
Third you have picking the faction you decide to tee off and then hititng their foragers and especially caravans, which usually yield some decent gear, money, and goods to be sold off.
Fourthly you have actually sending out the caravans yourself, which requires a nest egg to get you started and the ability to read market demands but which is by far the most lucrative non-fief source of income you can get. It's just that it can take time getting used to and it requires a fair bit of cash to get started.
Finally- if and only if your character is a dishonorable sort and you don't care about ticking off the public- there is the option to pillage villages and cart off the goods and money. It dings your honor, faction relation, village relation, and plenty more but the opposition is pitiful and the proceeds are generally good. I don't do this both because I don't think it's worth it. I like my honorable playthroughs both for moral reasons and pragmatic ones (given what honor does) because it undermines the productivity of the village you're probably going to want to rule at some point, and because I don't see the point given the more beneifical ways you have of getting it. But the door is open if you want.
Again, the carvan routes are by far the most lucrative, but I'd say a combination of the tavarn brawls, the missions, and the caravans are the best way to get your cash and skills together before committing to a faction.
When you finally have a decent stash of cash, make a Deposit at a nice, safe, out of the way location with a Merchant's Guilt (I like going to Finland in this case since it's at a far end of the map, there's only one approach, and I'm usually alligned with Sweden). That will slowly give you a nest egg that will accumulate money without you doing anything. The only problem is that you have to keep that town Damn safe, and it's more of a way to lock in your monetary advantage once you have it rather than a great way to make a fortune from scratch.
There are also some extremely lucrative routes shipping supplies between certain towns if you figure them out.
1. Roam around and do random delivery quests. With only yourself, there's no upkeep costs to worry about, and your map speed is so fast you can outrun any threat, even Tatar raiders. Attack every group of Looters you see because they don't have firearms or horses and so can be picked off with impunity.
2. Once you have 500-1000 gold, go to the southern portion of the map into Cossack and Tatar lands: Kyiv, Poltava, Cherchassy, Sich, Perekop, Crimea. Visit every city until you find one that sells Spice or Velvet for cheap (usually under 500). Buy one or two lots of it, but not any more, or you will be slowed down too much and not able to outrun various bandits.
3. Take the goods to the north end of the map - Sweden or Russia both work, but I prefer Sweden, because it seems more heavily populated and therefore better patrolled, so less risk from bandits. It's not not critical, though, because by far the most dangerous part of the route is passing through Crimea and southern Cossack lands. Once you are north of Kyiv, you are pretty safe.
4. Velvet and Sprice sell for up to 1000 in northern cities, so you should have made some profit. Keep trading like this and use the money to expand your business without compromising speed to much - add extra horses to your inventory, get a few companions and get them horses, etc.
5. When you have at least 10000-20000 gold, it is time to send your first caravan. You have to be very strategic about it, because unlike your own small-scale trading, a caravan will slow you down and you won't be able to outrun most threats. So there are two ways to solve it.
5 a. Get more money and hire 30-50 soldiers into your party for protection.
5 b. Find a city far enough north to originate the caravan from, s.t. you avoid most bandits, and then just pray that you slip through.
I usually do a combination of a and b - I don't hire enough men to be perfectly safe, but enough to deter or defeat smaller groups, then I play the odds and hope I don't run into a big group of mounted deserters.
The reason you were waiting until 10-20k to send the first caravan is that your first caravan actually pays you double, so you want it to be size Large and you want the goods to be as expensive as possible, so Velvet or maybe Spice in the most expensive northern city you can find (use analyze local prices feature in the city of origin, it'll tell you best route is).
After brining in my first caravan, I ended up with 120000 gold.
6. With that money you can outfit your company well enough to make these caravan runs almost 100% safe.
7. So keep on doing the trade runs until you have more cash than you know what to do with.
8. When you do, deposit it in a safe city (or spread it across several safe cities) for interest. Now you have a weekly supply of money to pay for anything you want, which will continue as long as you keep the city holding your money safe.
9. Defend that city no matter what!
10. ???
11. Profit!
When i first started playing this game i was like you. Hated the fact that I couldn't own my own business. Money was tight. But it is really easy to make money once you get rolling. All you need is property. Capture land.
Start out by escourting your own caravans until you have an army big enough to take a castle. Once you own a castle and a couple farms, you're all set. Fully upgrade them and protect them from looting. Take another castle. And another. Don't go to war with more than 1 faction at a time. Or they will keep killing your income by attacking your farms. Pay off the other factions that want to fight you, just to keep the peace and keep the farms/castles producing at maximum capacity.