WolfishMusings,
I don’t know why you have such a burning desire to host a pity party for yourself at the expense of the honor of your parents, but please try and be sensitive to the feelings of other posters in the CR. You are not the only BT or child of a BT in the universe, and your publicly aired extrapolations of the words of the Chofetz Chaim to your personal situation can be hurtful to other BTs who have equivalent situations.
If you are truly worried about your spiritual standing, pour out your feelings and specific case to a trusted rav. Don’t ask him generalized, obfuscated questions and then extrapolate the answers to your specific case. That’s not fair to him, or to you. You wouldn’t handle a medical, plumbing, or electrical question that way, how much more so a spiritual question? Yes, we have the mishna, gemara, rishonim, and achronim, and those words are true, but Torah is best found in the mouth of a living and breathing rav. That is the proper way for the wisdom compiled over generations to be applied to you personally.