with spending like that if a decent chunk comes from savings rather than income, you probably qualify for MassHealth.
I'm not sure if I'd apply in any case. I feel like it's questionable ethically to take public assistance when I could earn a high income if I chose to work for an employer.
* this is where you can usually tell someone is judging
And your metaphor of the poor as children you wouldn't steal candy from is exactly the kind of ideological superiority i'm talking about.