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As for the armor as it is the only upgrade you get until near the end of the game it is advisable to get it as soon as you can. If you clean out chapter 1 in terms of quests and loots you should have enough orens to buy it at the start of chapter 2 after the initial quest there.
I has to learn poker and sell rather rare valuables over long time
But may be guys know better
Easiest way to make money is probably gambling. E.g. the dwarf in the pub in Chap 2 gives you a lot of money and I feel like he is easy to win against (maybe I was just lucky though). Theoretically you can even kind of cheat with that if save the game, then always bet the maximum and reload in case you lose.
Also if you buy books, read them, then sell them back as they are useless once you read them. This reduces prices of books by 20% I think.
And from Chap. 2 on you can make a ton of money if you are willing to grind by fighting some of the people that attack you during the night, take their weapons, sleep until the morning, sell the weapons, sleep again until night, repeat... I think the weapons of the dwarfs pay most, just wait until one of them dies. It's pretty boring though, so I never really grinded it.
And obviously side quest are useful as they give you extra money. I think the hunter in Chap. 3 pays very well.