Is there ever a time when sin is more righteous than the Commandments?

Oh, you want us to choose between "The lesser of two evils" and "Two wrongs don't make a right"? First, drop that word "righteous". Only God is righteous. No human is righteous, in and of themself (Romans 3:10 & Isaiah 64:6-7) There is nothing righteous about any lie. As for 'more righteous' (than something else), that too is a misleading idea to apply to the choices you give.  But given your last update, there's no point in saying any more.

Sometimes a lie is necessary, such as to save a life.  That doesn't make it good.

Didn't Rahab lie?

When lives are on the line, lying is okay with God.  For example, verse 19 below is a lie.

Exo 1:15  Then the king of Egypt said to the Hebrew midwives, one of whom was named Shiphrah and the other Puah, 

Exo 1:16  “When you serve as midwife to the Hebrew women and see them on the birthstool, if it is a son, you shall kill him, but if it is a daughter, she shall live.” 

Exo 1:17  But the midwives feared God and did not do as the king of Egypt commanded them, but let the male children live. 

Exo 1:18  So the king of Egypt called the midwives and said to them, “Why have you done this, and let the male children live?” 

Exo 1:19  The midwives said to Pharaoh, “Because the Hebrew women are not like the Egyptian women, for they are vigorous and give birth before the midwife comes to them.” 

Exo 1:20  So God dealt well with the midwives. And the people multiplied and grew very strong. 

Exo 1:21  And because the midwives feared God, he gave them families. 

But because the lie was in order to save lives, God commended the midwives.

Stealing to give to the poor is a sin.  You should work in order to have something to share with the poor (Eph 4:28).

As sin is a religious delusion, the question makes no real sense.

“No one is bound to reveal the truth to someone who does not have the right to know it.“ (CCC 2488–2489)

For example an evil person asks for your social security number.  They do not have the right to know the truth. A tax preparer asks for your social security number to do your taxes, they do have a right to know the truth

This also means there can be cases in which it is morally licit to reserve the truth. Avoiding giving the location of people in danger of being murdered would be another such case

https://www.catholic.com/qa/is-lying-a-sin-if-done...

Sorry, Tay, but lying to authorities is breaking the Commandment. It would be better to say nothing at all. The Nazi's would torture you anyway & you will tell them the truth. They had ways to insure that.

Hmm... You could say that God is an Act Utilitarianist, instead of a Rule Utilitarianist. He won't be like: "You lied to Nazi's back in the 1940s, old man. You're going to hell!". Instead, He would be very understanding. 

Concerning stealing valuables to give it to the poor... who told you that the person you stole from was rich in the first place? Who told you it was their item in the first place? What if the person you stole from was actually someone who was also very poor, but some kind-hearted rich man decided to be overly generous and charitable with them? Yea... too many questions to answer, the risk for each of them is far too large, and you still can't know for certain. I mean you certainly can't go to a person and ask them: "Excuse me sir, but are you poor? I'm asking this because I don't know if I should steal from you or not". Yea, this one is a definite sin. It's clear theft even if the intent at the end is good. 

Not 'more righteous' but 'as righteous.' 

"GOD made Him who knew no sin to be sin on our behalf, so that we might become the righteousness of God in Him." (2 Corinthians 5:21). 

Jesus actually 'became sin' as part of His work of atonement, thereby giving 'sin' two legal definitions. The original legal definition which results only in judgment, and the 'new' dual definition that results in righteousness.

That is the actual divine legal basis for what you are describing. However, this legal application must be 'inspired' by Christ Himself through the Holy Spirit or you are engaging in nothing but self-deception. You cannot just 'sin' and declare it righteous. It must be a 'justifiable' violation of the original law demonstrating itself righteous by neutralizing the power of evil. 

there is more nuance than people think, if you lie to save lives, that is no sin