Long time sleuther, first time poster. This is a very baffling case because we are coming up on three months now since the disappearance with no named suspects or arrests in this case by LE in spite of all the agencies involved. It is also baffling in that there is such a tight timeline in which this disappearance occurred. It seems like a very solvable case and yet nothing so far.
A few thoughts. It is believed by most that a hookup or meeting occurred through an online ap. However, it is quite possible that the meeting that took place that night was not done online. Maybe it was done in person leaving no digital trail. Caleb had been in and out several times in the early morning hours. The first time we see him with the dogs and other friends on the ring bell camera. Then we know that after the roommate went to bed, he takes the dog out again. We see that on the Snapchat sent to his sister. Maybe there was someone living in that apartment complex that has been secretly trolling Caleb for some time. He sees him out there alone with the dog; approaches him, and they agree to meet up in say 20 minutes or at 3:00 AM. Caleb puts the dog up and then orders the food to be delivered by Uber eats then goes out to meet this person. It could have been a sexual encounter but it just as easily could have been someone who lured Caleb with a free bag of dog food. Caleb saw no threat in this person. It could also explain why he left with no shoes, no wallet, no keys. Just a quick encounter. I have had a feeling for some time that the perp may well be someone in that apartment complex. Keep in mind also that the security cameras for the apartment complex were not working. The person who encountered Caleb may have been awaringe of that.
The second thought is an abduction. So let’s say Caleb does go out to meet the Uber driver. Again, quick trip no shoes, wallet, keys. Instead of hanging around his apartment for the driver he walks out to the gate/entrance where he snaps a photo of a foggy bridge. A couple of guys come along and see him out there alone on a foggy night. An easy robbery target. Caleb is forced into the car but he has no money, nothing of value but a phone. So now they have kidnapped this young man; they panic then kill him. Or maybe there is a gang out looking to deliver a message to someone and Caleb is abducted but it is a mistaken identity. Again, panic sets in and Caleb is killed. In both of these cases Caleb’s phone is taken and shut of by his abductors. I do believe that if he was taken against his will it was by more than one person. Caleb is a decent size person who appears to be physically fit. The one thing about an abduction is that no one reported hearing a scuffle. One would think that Caleb would have put up some kind of resistance.