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I usually let the AI manage trade for me. It will find the best trade partners for you. If you want to do it on your own, you have to find the appropriate trade partners, such as a nation you're on friendly terms with, have a similar governments, and has plenty or resources you are seeking. If you need money, try trading with the U.S. or any country flush with money. And try to trade a resource that they really need.
 
I don't know if it's supposed to be like that but everytime I try trading something for money (like 25 supplies for 0.1 money) it automatically goes from 100% chance to 0. Is it a bug?

When it goes from 100% directly to 0% (instead of slowly lowering the percentage) it means: the other country hasn't got the good to trade or needs it itself.

So to check how much cash is available for tading, I usually start with offering let's say 10 supplies (everybody needs/wants those) and then raise eg. cash to see when the percentage jumps to zero, then scale back again to what's available for trading, then I adjust the supplies I am offering.
 
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DH made it so you cant leave countries without vital resources by overtrading them.