Hi Charlie and good luck on your renewed journey.
About your 'humility' issue - reminds me of a story (or joke?): Once there was a bochur looking for a shidduch. He had "alleh mailos" except that he was a "baal gaivoh". So every shidduch that was proposed, he would turn down and say, "For a gelungeneh bochur like me, you redt such a plain shidduch?!"
So as he was growing older, with no shidduch good enough for him, a shadchan advised him, "You're a great guy, but you have one problem - you're too much a baal gaivoh. You need to work on your humility". The bochur realized that this was his problem, and agreed to work on it. For a couple of months he learned mussar and worked on his humility. Finally he decided he is humble enough to give it a try. So he went back to his favorite shadchan. He explained that he worked on his humility and is ready to hear a shidduch suggestion. So the shadchan figured, since he's now humble, I can redt him one of his old rejects and he may accept it this time.
But when the shadchan proposed that old shidduch, the bochur was highly insulted and said, "If I rejected this when I was not yet so perfect, now that in addition to all my mailos I'm also humble, this is what you suggest for me?!"
Nimshal: When working on our humility, we still need siyata dishmaya to have it work for us.
Hatzlacha
MT