Fellow 'urban nomad' here.. an exhausting but fascinating existence to say the least. I was just in NYC a couple weeks ago. Stay warm, friends.
Just an FYI, Plattsburgh, NY follows a "housing first" model for homelessness, meaning if you go to that city and apply as homeless with DSS (which is a nightmare in itself, for me, anyway) they put you up in a hotel room (there is a limited time they will provide assistance to you supposedly, but as long as you comply with their abundance of rules you will be able to find a landlord before your time runs out) and you have to attend weekly appointments, but you are given 1st month and security deposit assistance (usually only 550-650$/ per person), and a second agency will furnish your new house/apartment with sofa/bed/tables/chairs/lamps etc. You are responsible for finding a landlord that will accept the DSS payment, (which can be a challenge, and sometimes their payment comes late, try explaining that to a landlord..)
It worked for me once upon a time, spent a little less than two months in a hotel, got a job, then found a house and landlord for 650$/mo in the center of Plattsburgh. It's about 70$ to bus up to Plattsburgh from NYC. Just an option if you get tired and want to move on/start over in another city. I often feel like that. The stress of life on the streets often tears couples apart, but it warms my heart to see you two staying positive through it. Peace!