Chris,
your pup sounds smart and eager. i thought id throw in my .02 on what i perceive to be 'acceptance' and 'impatience' in your dog. i don't know if my suggestions are in line with what you are training your dog to do... but, for what it's worth....
i think instances like his reaction to the kid on the skateboard show some uncertainty mingled with him trying out an 'i can scare you away' approach to deal with it.
Sounds to me that you have done things to build his confidence and he is curious/wants to investigate. he is going forward of his own accord. this is good, in that it shows his acceptance (confidence) in the situation. but in a way, its bad in that he is making his own decisions and judgement calls - he is too young for this. My thoughts are, as he goes forward and gets to the target, he then turns to puppy mush - he is not mature enough to carry through on his approach and this causes conflict for him.
What will happen as he approaches adolescence and adulthood? he will probably get more confident in his approach and carry out his intent (whether it be fear based or confidence based) You want to make sure he defers to you or uses his own judgement wisely
so,it's at this point that you can incorporate obedience - which will instill your leadership, build his confidence up further and teach him patience. Instances like his reaction in the crate show his impatience. he wants to go forward NOW! when you have him meet a new person, have him sit/stay for an appropriate duration, then give him the release before he can go forward. Or invite the person to say hi as he sits. Don't let everyone come up to your dog, you choose who. this should sort of relieve your dog because you're calling the shots and not forcing him to meet everyone , because he very well may not want to. If he understands you make the decisions on who to bark at and who to accept, then he will be relieved and glad to go by your guidance. Again, this may be out of line with your goals for your dog, i don't know.
im just thinking that some direct leadership in the socialization efforts would comfort your dog. remember he is just a young'un still.
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