Go get to know real homeless people, we are not talking about homelessness here. Though I think the OP is taking it a bit far, I think it would be fine to do it for a week or something if you opened up a huge opportunity for you.

There are a lot of people that I suspect you would consider "real" homeless that live out of their cars.

The main difference here is that I assume he is making decent money. More than you would expect of someone that is "really" homeless anyway.

You can be house-full and yet still homeless. Dwellings are becoming more and more just that, it seems. Not a "home". Not a Fortress of Solitude, if you will.

So why keep up the charade if you're out of the weather anyway?

There's a saying. Anything which was said before a but doesn't really count. I think this guy has a point.

I don't think in that context it represents an apology or even empathy. It means "allow me to politely tell you that you are full of shit!"

Kinda like saying "have a nice day" to somebody who was just rude to you.