Personalize it as much as possible.  Homeless is a Very broad category, say like African American, Hispanic/Latino, GLBTQC..., etc.  Could be sheltered homeless (i.e. staying nightly, semipermanently in a hypothermia shelter which ends in spring (April 1 is no joke: all out, no other options, learn mechanics, sales, accounting, customer sevice, green living, where to recycle x,y,z, basic $tools for indoor/outdoor/social/etc survival, etc).. and/or other place not meant for human habitation (doubled up in studio, basement, shed, squatting, so on the floor (pad/tarp/mobile TinyHouse, old ratty kid trailer now best for cargo/shelter move?), likely overcrowded and needs to get away to a quiet friendly place, alone or not, low stimulus time like autistic movie options, there are bike geeks, like train/plane/maglev/history/electronics/gamerz/...), domestic violence shelters, camping out, so full touring gear, on to someone to talk to about bikey things ( could I bike xcountry, what's Australia/Africa/Europe/China like to bike across/in, always wanted to visit my homeland/ancestral home, see the real skid row, Bowery, CCNV Mitch Snyder story, where Solo was filmed, 50¢ lived here, etc...). 

Homeless category can include kids who, because of circumstances never got a bike, parents never learned to ride, so can't teach, etc...  Bike Rodeo, keep up with other kids who can afford like some places require you learn, like gym as many $ports as available... On up/down thru drug addiction, will sell anything donated [or not] for high/etoh, something needed more, bus ticket home to reconnect to family, estranged x,y,z, some year reunion or just someplace warm/cold /different/ always wanted to go, never got to, etc. 

Mental health issues also common, say anxiety, nervous about falling, bent different, quad/pedalcart, aged, beach cruiser, low rider creation/pimp my ride, etc. 

Court involvement, record expunged, etc. 

So many needs, a stocking, cookies (diabetes?), clean underwear like lost grands/momz used to give, etc...

Been thinking an old bike frame makes a nice tree:hangs stuff, reusable/green, bells hanger etc, on thru:i become less Christian each year with focus on commerciali$m, when can't buy much for others, therefore excluded... make me a back fork stool, chop up old frames and atomic zombie something adult bigwheel like, etc...  But don't like stick arc welding, tig , mig OK...  No place to legally weld yet.  AWS low income /student like membership...

But I digress into cryptic diatribes, especially when tired...  May decrypt when rested better...  Hopefully on regular keyboard..

Chemical hand/toe warmer packs, assuming safe with them...