1. You can get healed for 20 by resting once. It happens when you rest on tile with bonfire icon.
2. Successful foraging probability gets higher when you learn Forager perk. But I never do that because I found ways of not foraging.
3. I think there are no enemies that don't let you win with 0 Dignity. There was Dark Knight, but it was changed. Basically every such occurrence now is avoidable by spending Willpower, and I personally also never ran out of it at least.
4. If you spend 15 food for scouting, it seems you don't have enough Perception. It should be 5 to play comfortably. If you are struggling with getting high Stats, you definitely should farm some achievements in Iron Man mode, then access Beginning Bonuses (look them up on ToA wiki). Also there's +1 stat armor you should buy.
5. Money are not really scarce. They're just not farmable, but one-time gigs. This game is working the way you have to suffer some failed walkthroughs to memorize each one. I will give you a list:
• Brothel Madame quests - 150+120 gold
• defeating Ogre once - 50
• Arachne with Perception 5 - 50
• Felling Quetzal quest - 300, claim on Town Square
• Travelling to the end of Verdant Valley - 100 + gauntlet that saves you 50 because you don't buy it
With those money you can buy all the food you want. Plus gear like best armor and weapon.