Notpashut:
1) Actually, you said “It just so happens that the Chofetz Chaim (Klal 4)says that one SHOULD speak Lashon Hara about the type of person you describe.” The SHOULD is saying that I am SUPPOSED TO speak lashon hara about her. No one else knows that she eats out non-kosher so how would that affect them? I personally disagree that me speaking lashon hara about her would NOT push her further off the derech, but since you dont know her, I will have to ask you to trust me on this issue.
2) Perhaps this issue is one of semantics – when I say I don’t judge them, I mean that I see what they are doing wrong, don’t do it myself, but dont judge the reason they are doing it. That is up to Hashem to decide how/if they are guilty. Does that make sense?
3) I never said that driving to shul on Shabbos was ACCEPTABLE. There is a big difference between accepting what someone is doing, and finding it acceptable. I accept that for a Conservative person moving towards Orthodoxy, driving to shul might be extremely hard for them to give up because they grew up with it being ok. If asked, I would tell them that I always learnt it was not acceptable, but to speak with a competent Rabbi. But its not my place to “judge” (again, a semantics thing) the person for driving to shul, but I would make sure not to follow in their footsteps.
4) I dont try to justify their behavior (giving an explanation is not JUSTIFICATION), just to understand that everyone struggles with different things. I have a feeling if we were having this discussion in person, you wouldnt feel this way about me.
5) As I said in this case, my friend is not spiritually endangering others, just herself.
6) The difference between cheating on taxes and eating out at a non-kosher restaurant is this: cheating on taxes is STEALING FROM MILLIONS OF PEOPLE. There is no way to slice it differently. You are stealing from both Jews and non-Jews. You are stealing from poor people who need food, the health care system, road maintenance, Police, Fire Department etc. My friend is doing something wrong on a personal level that will generally affect her and her ONLY. The attitude of “whats not nice we dont show” is a level of hypocrisy that definitely puts people off the derech.