I don't think it's healthy let alone desirable to discourage pointed questions from kids. It's another thing altogether to teach them to be tactful and tip-toe in mixed company around sensitive topics (which goes beyond the level of maturity of a child), but they shouldn't have to do that with their own parents.
Reframing a question isn't tiptoeing around it: "that's a Wrong Question" is the start of an answer. Though, probably the kind of answer you'd give someone able to read The Ask and the Answer and realise it's about fascism.
Answering with a "Why don't they? What's keeping them from doing so?"-type reframe is the better approach for people not used to making such leaps on their own: you're teaching them to do this reframing, and to question premises.
(Wrong Question = question from an invalid premise)
No. The problem is not whether X has a job or not. The problem is why X was forced to lose their home. In this day and age you can still lose your home even if you are juggling multiple jobs.
Not with geared-to-income housing that one rents. A house you own, yes, but the outcome of no longer owning a home does not translate to homelessness.