You wrote about this very intelligently and insightfully. Yet I have seen evidence of some kind of disorder in your very faulty thinking about certain concepts. So, as for what is going on with you medically, I hope a doctor can help you figure that out.

Both you and your brother have never had a gf at ages 26 and 28. To me, that's strange, and I wonder what's really deeply underlying there.

While I think you can't tell your brother not to outshine you around friends, I do agree that asking him not to get a job where you work for your sake is perfectly reasonable.