Matthew - Both of mine do the crying thing occasionally. Generally if they are scared, like when we go into the vet's office and the last time they were there they got shots. Mine also enjoy the car and definitely do recognize places we go (my mom's house, the park, the groomer) and they perk up and get excited even if we went a different way to get there. It's VERY possible he recognized something in that area and got scared, especially if he was otherwise riding fine in the car.
We got our 2nd Yorkie, Sammy, when she was about a year old and she was a re-home. It took her a week or two before her personality came out as well. Just give lots of tiny treats and he will come around. You are doing a very good thing!!
He looks to be the same size as Sammy (6 pounds) and she eats 1/4 cup of dry food 2 times a day. The tummy issues were very likely a combination of new food plus stress. Yorkies have sensitive stomachs. You might try an inexpensive premium dry food like Canidae if you find he has loose stools. As much as mine LOVE canned food, they have to eat kibble for one of their meals or they have bad gas!
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