What we had and didn't
Years ago we didn't have an iPod, htc desire android, or other nifty toys we do now when we were on the streets. Back then we did it the old fashioned way at best with a Pentium2 type laptop. WiFi was ridiculous to find free.
But over time things improved online for many people experiencing homelessness, much like how the businesses delivering service to them directly did. The problem isn't people getting 'out' of homelessness, it's stopping the cycle of the chronic and cyclic homeless.
Regardless how portable or interconnected any of the new gadgets are to bridge the digital divide to the masses, the stuff will fail every time when it's caught in the rain on a dark night no matter how much awareness is brought to it.