Thanks for not taking it personally and going off about it

I think you've got a good idea there with getting one now and letting it get used to bike life.
One really good thing you can do now, is get yourself food stamps. It's good to have that extra biut of income set aside just for food, but also, as soon as you get your award letter, you can use it to apply for petfoodstamps and the dot org site.
They don't send you money for food, but rather the food itself, once a month. If you don't have family that can do it for you, find a friend who let you apply for both with their address, and who wouldn't mind forwarding the goods to post offices along your route once a month. I haven't had a stable address in years so I never applied, but I've heard it's pretty damn useful if you can get it to work. The trouble, I think is that the people who need it the most, often times don't have an address, and that's a requirement for the organization.
On the plus side, if your dog has special dietary needs, they can accommodate that. They work through an online pet food and supply store, that stocks even the really high quality foods like blue diamond and taste of the wild! The latter of which I recommend for dogs above all others
I agree though that a lot of "road dogs" are shady people, a dog is far better companion in that sense. Just make sure you also spend a lot of time with the dog before getting on the road. Training and bonding are crucial. You don't want to have to worry about him getting so stressed at any point that a snap/nip is his answer to ti, and you certainly don't want to have to worry about him taking off for lack of bonding.
I've known a handful of good dog owners in this lifestyle, and they all make a really special effort to treat their furry kin like their own children.
And walking around with your pup with their own pack vest, carrying their food and toys, is fucking adorable. So metal.