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