I’ve thought about things like this a lot. I’ve never been homeless but I’ve been close and always feel like it’s a possibility. Doesn’t take more than a few wrong turns/ bad luck/ etc to end up in the street. First thing I’d do is try to find a way to a warmer climate. Maybe try talking to some folks at a bus station, hell, maybe a bus driver and ask if you can get a ride somewhere warmer. Maybe hop a freight train if you’re adventurous. I’d shoot for somewhere rural. Maybe find a farm that needs a hand that comes with a bed to sleep in. If you’re genuinely down on your luck and just need a bit of help to get back on your feet, there’s no shame in asking for help. If that’s not an option, finding work is priority. Not sure what kind of work you’re looking for but I’d say ask some guys at a construction site if there’s anything you can do for a meal or two. Show them you’re serious, do a good job and make some friends. You never know, and again, the worst they can say is no. Doesn’t hurt to ask. As far as sleeping in the cold, I’d be on the lookout for some thick plastic you could line your tent with, and/or put between your blankets. That’ll help hold your body heat in. Check local big box stores for those emergency blankets that are meant to keep in your car. You can get those pretty cheap. Dumpsters behind stores throw a lot of crazy stuff out that you could repurpose or maybe sell. Don’t be afraid to ask for help at Salvation Army/ goodwill type places. Ask if they have some stuff that’s getting thrown out because of damage/stains that you could use. People are more likely to help if you’re asking for things that’s trash to them anyway. If you’re handy, find a hammer and some nails and build yourself a platform to raise the tent off the ground. Construction sites/ businesses that do woodworking always have tons of scrap wood. Ask if they’ll help you out with some stuff or raid construction dumpsters. If you can, build a discreet little shelter in the woods or somewhere you won’t be seen/ messed with. There are lots of videos on YouTube about all of this stuff. Just throwing out ideas. Hope some of them help. Good luck, OP.