Dean knew which skills he needed, and he knew how to get them.
Dean looked up to Mrs Garibaldi and was encouraged by her smile and nod. Everyone who lived in their current home, a mobile home colony at the edge of town in the middle of nowhere was poor. But their neighbor still managed to feed her 6 children, she clearly was the perfect person to teach him frugal cooking. There was a time when people had to learn to do more than just warm a can of soup or prepare orange Mac and Cheese. Starting with the things that were cheap and filling to which kinds of meat were cheaper and what you could do with them. His notebook was filled with tips, instructions on what to do with leftovers and how to stretch his provisions.
When they moved again and Dean had a second pack with him his father wanted to protest. He looked inside to see a few spices and dry food, a few cans of vegetables and meat and some powdered milk. A notebook.
John Winchester looked to his 14 year old son and gave everything back to him. A simple nod in acknowledgment was enough.