I think parent is right to point out that remote/contract work is more tenuous than the alternative in most cases. I also found your comment aggressive and nasty... the irony of the "stop being negative" put-down.
Your comment above didn't come off as negative to me fwiw. I had the same reaction.
The error in thought is limiting his perspective to people he knows personally, which of course can make it seem unlikely or impossible. For example, I don't personally know anyone who lives and works in Silicon Valley and doesn't struggle to make a living, but I do understand that it would be possible for me to try to do so if that was my desire.
I think he is mostly correct though. "If you have a good resume and live 30 minutes outside even a small town, but you also have to drive everywhere" isn't really comparable to the "standard deal" in a city.