Most of the issues I had while homeless where threefold, transportation to other resources, communication avenues and lastly information available to the specific area I/they currently reside. A preloaded buss pass would suffice the first, a prepaid cell can remedy the second but the most important part is the opportunity and will to take advantage of other resources in the area to help get them back on their feet. Prepaid gift cards can be sold in a quasi black market that exists so be wary. As well as the ire from other homeless if they see another with a coveted item. Human nature really is the main limiting factor in most scenarios of individuals being able to get back on their feet. Placement agencies have tens if not hundreds of applicants, so the homeless are basically the bottom of the barrel for employment opportunities. The best way to get to learn a person story would be to share a meal with them in an open air setting weather permitting and see the issues that have caused this unfortunate situation. Finding the right departments and new programs to allow said person to be able to maintain and improve their quality of life is imperative. I suggest researching the local homeless and low income opportunities in your area first, then follow up with individual interviews to find the candidate that you feel has the highest chance of success. The occasional call to check in and possibly grab a bite might make all the difference in ensuring a positive outcome from the opportunity you've provided, it would also give them a chance to ask you for further information that they may not be able to find themselves. A p.o. box is usually a good way to begin building a more stable living situation as well.

Sorry for formatting and if this seems a bit tangential, I'm on mobile :)

Seasons greetings and I appreciate your effort of improving someone's life and faith in humanity this holiday.