First, dont ever take your chances on the devil, vampire, and the magic dude

Second, NEVER EVER let the candy girl in your kingdom, reason is that she will keep saying "I stayed up all night eating candy can i have some gold to go to the doctor

Lastly, let the knight have the sword, cuz bad things would happen

Last BUT not least, help the robot, after lots of days later, he will give u something, you could sell that something for 500 gold coins

I think the wizard dude can be great for early game, cuz the gamble can be worth it.

i cant agree abt the magic guy cuz he gives me BANK

From 1 playthrough, my tips are:

• Dont care about money as much, HAPPINESS is the way to go
• Whenever you go into the negative with money in early game (below like 1000 people), just decline any deals for money, EXCEPT the knight. He will always come around eventually and give you 100 gold for free. If you're really below, do this multiple times.
• Never accept the wizard, the top price jester (700 gold) or the vampire
• If you angry the tree people,  don't pay them the first time and when they come again, just apologize
• Accept EVERY opportunity to build a shop or any of the sort (earns you money in the long run