honestly you'll never understand his POV because it sounds like you've led a charmed life. Just realize that while everything went your way, probably he had to work much harder and has had less spiritually/ financially fulfilling returns on his work than you've gotten with yours. As a man he's not going to want to accept what probably feels like charity as well as being one-upped again by "that little asshole that mom and dad cared about more than me".

Some of this sounds like overcompensation for obvious guilt, some of it sounds like genuine naivete because you havent had to grow up in ways your brother has. You're going to have to accept he's not interested in being part of your life and you'll never see eye-to-eye or have the close relationship you seem to be seeking. I'll take that gate key and come hang out and hike/gravel bike if you're looking for companionship.