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Only played the game for a few days. I figured out that shields are important, at least early on. But as your troops level up, there isn't enough in the crown rewards and such, to keep your men. I am constantly near broke or broke. And heaven forbid, I get a caravan duty that is 5 or 6 days, that will pay 2800 crowns, because my men start deserting on the last day or two.

The monetary system in this game seems WAAAAAY off to me.
Different settlements will give you different prices for different goods. There's a settlement-wide general price multiplyer, and then specific goods can be more or less valuable depending upon how abundant they already are. Shop around for the best prices before dumping your loot. Also consider pursuing alternate sources of income to missions. Raiding wilderness lairs can be lucrative if you manage to survive the experience.
Getting high relations with settlements improves the prices you get for goods you Buy and sell. Equipping your bro's with a dagger or flail and using the secondary attack on surrounded human enemies is a good way to get good early game armor, saving you a few crowns.During contract negotiation try asking for more crowns, but be careful asking more than once it can affect relations with the settlement, thus making you pay more.Also cavavan jobs typically suck, your a slow target, after a battle you can't camp to quickly repair and heal before the next battle and you spend a lot time doing nothing which can be better spent raiding ruins and leveling up your bro (if they survive), unless your running low on food, planning on going to the settlement that the caravan is going too or going to a village with trade/tools/arrows items or settlement with high quality armor and weapons for sale to get that sweet well supplied bonus, it just is'nt worth the effort.