Joel strikes me as a confident dog, and I think that is half the battle. He will want to be with you whenever possible, and that is probably why he whines when you go out to shovel, but accepts being separated when necessary.
I wouldn't worry about him choosing to be in his crate when he is left with another person. Is the other person entertaining? Max would love anyone willing to play fetch, but if the person is boring, he would just go to his bed.
