It sounds like he wants to trust you, so that certainly helps! Plus being food motivated makes it so much easier. Is he your only furbaby right now? I think feeding outside the crate sounds like a good idea, although I would gauge his reaction before moving it father every day. It's possible that could be a little too fast for him, depending on how much farther you move it.
Five years ago I adopted a rescue when he was approximately 10 months old. Fortunately, he trusted my husband and me immediately so I was surprised at his reactions to other people. We don't know his history except that he was rescued from a kill shelter in Alabama before being brought with a bus load of dogs to MN. He got along well with our senior female dog we had at the time but she is the only one. He hates all other dogs. Initially when people tried to approach him he would show fear and do his best to hide behind me as far away as he could from the person. Then it changed to actively barking, lunging and growling to keep people away. That behaviour has improved with a lot of work, but he still doesn't want most people to come to close and definitely not to pet him. With him, the only thing that has worked for him to accept new people is for them to completely ignore them. No eye contact, no talking to him, definitely no touching. When he first met my parents they ignored him for the first couple days, just letting him take his time and do his thing. Toward the end of the second day he came up and sniffed my dad's hand. Dad thought it was my female so he went ahead and petted Cyric. Cyric has adored him ever since, and he completely accepted my mom as well. There are only a few people he has let in his inner circle but once you're in it's solid. He hates my brother for some reason and we're not sure that will ever change, especially since he only sees him a couple times a year. So all that to say, maybe your little Boston just needs some more time listening as you go about your day, maybe talking to him but not petting him, letting him come to you once he gets curious enough and a little more bold. If he was being attacked by his housemates he may be scared that could still happen at your house. For him maybe three weeks isn't long enough to trust that he's in a completely safe space. Cyric has taken a lot of work, time and patience and he still wears a muzzle when we walk bc he is unpredictable with people and would attack a dog if it got in his face. The muzzle was recommended by the trainer we used and it's for Cyric's safety as much as anyone else's. I have to kind of protect him from himself. I don't take him walking where I think there may be loose dogs that could run up to him, trying to show him I will protect him. That isn't always easy, of course, bc sometimes dogs just get loose, but I do the best I can.
I am definitely not an expert, just sharing some of my experience with a very fearful dog. Hopefully all your little guy needs is just some more time. I know you must be a very patient dog mom based on how many senior dogs you have rescued so I'm confident you have what this little guy needs. I hope he realizes that soon too! Best wishes!
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"No matter how slow you go, you are still lapping everybody on the couch."
"God, please help me to be the person my dog thinks I am."
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You don't have to be fast, just keep moving forward.
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