So I'm not a homeless person nor have I ever experienced it. But there are various homeless sites I've seen across the internet.
The general recommendations I've seen are:
1. Get a good smartphone, its required to get a job these days.
2. Get a gym membership so you can get a place to shower and look good for your potential jobs.
But smartphones are consistently on the recommendation lists for the homeless. Its not a secret, its their life. People in poverty already know the importance of smartphones.
In my experience: its more useful to ask questions from people actually living in homeless / poverty conditions. They tend to know more about homelessness / poverty than people who have never experienced it. In general: people who are on poverty websites / homelessness websites are incredibly resourceful and understand how to play the long game very well.
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In any case, short-game vs long-game is a basic issue that's understood at all levels of wealth. Some people are just bad at playing the long game.
But in any case, a good phone, with up-to-date internet access to keep connected to today's workforce is ABSOLUTELY necessary, even at the lowest levels of poverty (ie: homelessness) in today's culture.