Hey TB, I feel badly for you, but I think you've found your way to some very bright people here on the board - hopefully they can help out.
I have shades of the same concerns as you. I'm older, 69, but am in good physical shape; also on TRT. I have only a limited response to Viagra so I tried Trimix, with the same less than ideal erection quality. My urologist is also thinking venous leak. I tried the rings but they don't make much of a difference.
The kicker, to me, is that I often wake up with a super rigid erection. Hard to believe that I can't get an adequate erection during waking hours, even if I use Viagra or Trimix, but then in the morning I'd wake up with a 10/10 erection. Maybe many things are psychological in nature . . .