How come it always seemed like he never had any money, even after he started working for Angela? We in one episode, learn he was the highest paid housekeeper in the neighborhood. Plus, he only had his old van , didn't have to pay rent, and had no food cost or utilities. And yet, he couldn’t spend $250 for a ski trip or $45 for drill team uniforms.

Admittedly, he was paying his father's rent that first year. And the later seasons, he was also paying for his college. He was presumably, also setting aside money for Samantha too. And Tony would still need to put money in insurance and gas for his van.

I think it was because he was a working class guy trying to live and raise a child in a wealthy neighborhood, and trying to give her some of the things her friends had. In that ski trip episode he told Sam "I don't make the money these people do!" And in Housekeepers Unite (the one where he was the highest paid housekeeper) we can see that all the housekeepers don't have the kind of money needed to live in that neighborhood. Angela loved him and loved Sam so she paid him more to help them be able to fit into the community a bit more. I think she essentially treated them like they were her family more than like he was an employee, or like they would be if they were married, but kept it on an employer / employee basis so it wouldn't be like an "allowance" or something. There were plenty of times she wanted to pay for something for Sam or for him and Tony would not let her. He and Sam were treated as family whereas the housekeepers Angela had before him and the others in the neighborhood were just employees.