moish, your question is deep and important to you. I don’t really understand the picture you are painting very well, but I can commiserate with you on life’s unfairness. The bottom line in any situation is that life is not fair (and that’s not fair either) but at least it is unfair to everyone.(?)
Some people will act like nothing fazes them, but they suffer privately as much as anyone. Others will feed off any little excuse to whine about how sad their life is and play the sympathy card. It’s all an act. Everyone has their ups and downs, their good times and bad times, their challenges and their days on easy street. The face we put on to the world is just a show. (The only exception to this is someone who is on a very high madreiga and literally lives the phrase “Gam zu l’tova”, but these people will never bother you)
As for judging others, sadly this is a fact of life too. Of course we shouldn’t but sometimes we do, and the irony is that the person we are judging could do the same to us in a different middah or action. No two people have the same temptation or inclination to do wrong, so it is impossible to understand why one person fails in an area that seems easy to overcome. I don’t know what to do about the “judges” except to ignore them as much as possible. That doesn’t help much, but I don’t know what does. At the end of the day, what they expect of a person doesn’t matter. It only matters what Hashem expects, and He knows each person’s personal situation.