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This sounds to me like a puppy that isn't getting nearly enough physical activity. You need to burn off all of that excess energy. Putting him in the yard so he can bark at passerbys is not a solution. Take him on a long walk (miles not around the block) or get him to a dog park and have him run around for an hour or so at least. Daily. He doesn't sound keyed into you since there is no interaction with physical activity that bonds pets with their owners. It is never to early either to start getting him socialized with other dogs and people.
Also, "Time Out" means nothing to a puppy and can't really be used as a form of punishment once they reach a certain age. They won't care as much about being left alone.
If I was in your shoes I would take the day tomorrow. At least one day but probably two just to stabilize things. There is no way to know for sure how you will react to this, but I can't see how being close to your family in this situation would be a bad thing. You may handle it incredibly well and have other family members that don't and you can support them or the opposite may happen. It sounds like people may be hesitant to ask you to come down because of your work schedule. They might be trying to respect your decisions and that is a good sign, but I would still want to be close to the people that knew him as well as I did especially if it is only an hour or two away.
The former came up recently after we played a board game with friends called Pervert which is a never have I ever type of game. I won and he came in last. It wasn't my game or idea and he seemed to think it was really funny at the time but later it was clearly bothering him.
Maybe you should try not playing games like this or find friends that have more diverse interests.
This. 100x this. The two examples you use are from situations that he experienced, not conversations that he initiated. I also think the wealth analogy is very appropriate. Obviously, a big part of a relationship is understanding your partner's insecurities, anticipating them, and reacting appropriately. This is a major issue for him and my advice would be for you to adapt the relationship around it. The fact that you are trying to solve this problem and are considering his outlook is a really healthy place to be, but I don't think trying to push him into sexual situations with a third person is the way to go. Nor are playing games like "I Never" and hanging out with friends that revel in this kind of discussion. My current GF does not appreciate gaming the way some of my previous partners have. It doesn't mean I'm actively trying to entice her, to change her, to "catch her up" in the gaming world. We share a TON of other interests so ignoring one of mine is not a big deal at all. Would it be great if she could sit down and play some Xcom with me? Hell yeah it would, but I'm not going to sacrifice her and the relationship with all of its other amazing things because we don't. Hope that makes sense.