There is a much much deeper question here. Which life is really better?
I took 10 months off where I lived with just two backpacks. I wasn't homeless by any means, I had my savings I was living off of (technically homeless I guess, but not in the cultural sense).
Even though I had a lot of expensive electronics, I didn't buy a lock until about 7 months in. Even then, a lot of hostels didn't have large enough lockers for my small back which contained my laptop, camera, etc.
There is a sorta social contract with backpackers I can't really explain. I still kept my stuff hidden, but I never had any real fear of people stealing my stuff.
Those 10 months were the best I've felt in a while. I was away from the cube. I was working on my own research (I wrote a lab manual for a friend's class based on some papers we wrote). I worked late into the night and walked around new cities every day. I was never tired, exhausted or irritable. I dreams of getting back into school and working on my PhD, but I'm still working on fellowship applications and I ran out of money .. so back to full-time IT work I went.
That "regular" life you talk about -- getting up early and working the 8-5 grind to get a paycheck just to keep on doing the same fucking thing day in and day out. That's bullshit. And that's coming from a software engineer who gets paid a lot and I have a lot of freedom in my work.
For those working low income jobs where they barely have enough and have to scrap and save every paycheck, that's super bullshit.
> For example, if you've been homeless your entire life, you've never had to lock your apartment door or carry a key around.
I live in a place with a massive homeless population and tent cities. People have their stuff spread out with them, but they have no fear of anyone taking it. Part of it is the poor looking after each other, part of it is if stuff is stolen, it's not like they have much to begin with. Suddenly you're housed and now you have something worth breaking into.
I'm getting a bit ranty at this point, and I'm not entirely sure what my TL;DR is. I realize being poor and homeless can suck terribly. But the things you mention...those aren't the bad things. Those are amazing ways to look at the world that are taken away when you try to bring civilization to the savages.