Traditional job, full-time van living, and pets

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I know this is an old post, but for others in the same boat, I worked full-time in an office for a few months last year while vandwelling with my dog. What I did is posted an ad on Kijiji (the Canadian version of Craigslist) looking for someone to watch him during the day, in the area near my office. I posted and said the person didn't even need to be home, my pup just needed a place to chill during the day. I offered $10 a day, so ~$7.50US. I got a bunch of replies, and ended up going with a nice woman on a pension who had lost her own dog a few years ago. I paid cash weekly and it was a good arrangement.
 
I don't have to worry about leaving my dog for work, but I've been worried about having to do simple things like grocery shop. As it is, I don't even like leaving him alone in my son's house. He freaks out. He has been by my side pretty much every single day since he was about 6 months old and he will be 10 this year. Before, he had my roommate Kay and her dog to ease his anxieties. Now, all he has is me.

My doctor can prescribe him as an emotional support dog, but legally that doesn't require stores to allow him entrance. Therapy dogs, yes.

Walmart, some Walmart's, have implemented an order ahead and they'll bring your groceries out to you. I am hoping that it becomes universal throughout their stores. That would make things so much easier, except I do like shopping at local Mom & Pop stores.

This is the #1 and almost only concern I have about hitting the road alone.
 

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