Your problem is you “go out of your way to ensure he is happy” . You are basically telling him he is the most important person in the world and you will cater to him. So of course he behaves this way …it’s his right because he is so important. Couple that with the vibe he gets from your feeling he is “brilliant” and he is now a brillant VIP and yet you are surprised he acts entitled like one.

Also your handing out of food to the homeless sounds like you are acting like “lady bountiful” and that it’s really all about the optics of being giving people. At 6 he is not going to understand how to be truly generous if you act like you are giving treats to the animals in the zoo.