Wow Nancy Grace is quite a character.. that's the first video of hers I've ever watched. Anyway, thanks for mentioning it, it was helpful in understanding the timeline a bit better and the reasons why some things aren't certain
1 a.m. – Caleb is seen on a Ring doorbell camera with his roommate, friend, and puppy
2 a.m. – Roommate goes to sleep. Caleb is preparing his fishing reels for the next day. This is the last time his roommate sees Caleb
2:44 a.m. – Caleb sends a Snapchat to his sister, walking the new dog
2:58 a.m. – Caleb’s phone is turned off, or dies. It pings at his apartment complex
3:03 a.m. – Caleb sends a Snapchat of the bridge to an old high school friend. From the Nancy Grace video around the 30:10 mark, Dad says the dog is back at their apartment at this point - they must know that somehow, and not just because the dog is back at home in the morning when Caleb is discovered missing, as Caleb could have had the dog with him at the time of the snap and then taken him back home after. Doorbell footage maybe?
3:20 a.m. – Uber driver seen on surveillance camera with Caleb’s order
So Caleb walked the dog at 2:44, sending a snap to his sister and took the dog back home. Then he went back out for some reason and sent a snap to his old high school friend. Why? What's the significance of that place? Is it somewhere he'd met that friend before? Does it mean something to them? Was he due to meet that person, or hoping to when they received the snap?