How do you manage hypos when on shots and oral?

What an experience you had PennStateDoc! Thanks for the excellent descriptions. Can’t imagine going through all that when first diagnosed. I only had very high blood sugars for a couple of months and I couldn’t stand it. I became alarmed thinking that my brother had been going through that for so many years! It’s strange but he seems to feel better when he is running high. I told him that I was feeling flashes and numbness and he had no idea what I was talking about. “Must be old age”, he said.
I decided to talk to him about this a couple of weeks ago. I asked him about correcting for the sugar he eats. He was clear: " I don’t have enough insulin to do that". So… after drinking so much OJ to correct the 2 hypos, he ran super high until the next morning when he was due to take his next dose. My thinking was that he didn’t have enough insulin to counteract what he was eating during the day and because the pills never did anything before the insulin, if they were kicking in now he would have no idea how to figure all the interactions out. I never thought about the fact that the insulin dose could be too high. Of course that would be logical but there doesn’t seem to be anything logical about this at all.
I don’t understand why the drugs have not worked for either my brother or myself. I think that initially my brother’s numbers went down and he was “stabilized” at around 20.
He said that one more recent drug had helped him to lose weight but then it had suddenly stopped working.
I found that ,with each new pill, my readings went up. I decided it was the side effects but the endo says it’s the “progression of the disease”. Could there be a genetic factor here? I have 2 cousins who took metformin and, as they couldn’t handle the side-effects, they just stopped. With little effort, they both have normal A1Cs. One of them said that she would be allergic to diamicron. Until I was diagnosed, I always had doctors who hesitated to prescribe so I only went about twice a year. When my numbers went down when I stopped the drugs, I started to rant on about pill-pushing. I still do.
What if that’s not the problem? Does my brother’s body fight to maintain a reading of 20? Did my sugars go high because my body was fighting the drugs? Has my pancreas shut down? Is this a honeymoon? I wish one of our doctors would at least try to figure it all out.