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I think you need to back up here .. you have a slight foundation (inside, with a trainer. So you need to practice and build on that foundation - start with practice inside the house (see those links I posted for tips on how to start). Then move to the back yard. Then the front yard. Idea is to begin with no- or minimal distractions, slowly increasing it. You can't expect him to jump from kindergarten to PhD level immediately.
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i would, but... tiny appartment, big dog, no front or back yards, LOL! ah, life in crowded montreal...
but yes, the training would be one-on-one with him, short sessions to start with, the ultimate goal being to walk him with his flat gorgeous leather collars that hang useless in our house (grumble grumble). hubby is on board now with the training.... that was the biggest hurdle!