Really? Sell a laptop and bike and you might have a couple of weeks rent at best. Stop buying cigarettes and dog food and you aren't going to magically save enough for a one-bed apartment on an ongoing basis.
Not really. In order to get in most places you need first/last/cleaning deposit and good credit. For that you need a job. But to get a job you need a permanent address, a place to get clean everyday, and fresh clothes everyday. But to have those you need a place to live. While it's true that "digital nomads" choose to be homeless, that is more often not the case. I went the digital nomad route and found myself in a hole that was hard to get out of. At least I still had a car to sleep in and a laptop. Showers were a big problem. The best solution is to join a 24 hour gym.
Not a chance in hell -- a laptop that will last at last two years goes for what, $300-400 ?A used bike goes for way less than a hundred. That would cover at most one month of rent, and then what?
Rent for how long though? One month? With no security deposit and no documented income? If you wanted to rent an apartment for one year it would cost $500/month x 12 months + security deposit == $6500. This does not include food, utilities or heat.
So no a $400 laptop does not approach the cost of rent.
300 dollar laptop =! Fancy laptop. There's 0 chance of the added cost of all these products being equal to rent. Even assuming its a fancy laptop, are you suggesting he sell his only means of income to MAYBE afford a month of rent? How bout the next month? Judging a homeless person based on their small amount of possessions in a single picture shows a complete ignorance to the situation most homeless people are in...
That's a ridiculously myopic application of the concept (which is flawed to begin with). Even if some needs are more important, that doesn't mean we can't make plans to better fulfill those needs in the future.