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I wouldn't feed a dog milk. They're lactose intolerant, it will cause stomach upset

As for the hand feeding, try what I did with my dog: feed her by hand, but move your hand closer and closer to the bowl each time, till you are resting your hand in the bowl, then remove your hand, but keep it touching the bowl, then move slowly back. This took about 2 weeks to do, not all in one feeding.
 
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