Great questions. Thanks for asking for clarification.
> I thought that Jesus was going to wipe away every tear? Isa. 25.8
Also Rev. 21.4. Oswalt says that the Isaiah verse means "God will take away the sorrow associated with death. Even Rev. 21.4 continues, "He will wipe every tear from their eyes. There will be no more death..., for the old order of things has passed away." Dante, in The Divine Comedy: Inferno, adds, "Who is more impious than that one who feels sorrow for God's judgment?"
> So how can a believer in heaven be punished? Or even think they are being punished?
They won't be. They may have regrets over the way they lived, but they will understand their degree of reward to be perfectly fair.
> But this judgment seems to be a one time thing and not ongoing for eternity.
We barely have a tiny glimpse of the ongoing dynamics of eternity. I find it difficult to comment because we know so little. We are told by parable that we will have responsibilities and lives to live. We are told that Christ will reconcile all things to himself, though we can only speculate as to what all that entails. But I agree with you that heaven will not be a place of punishment. I agree that concept has no biblical support. I don't see any teachings in the Bible that describe heaven in any kind of negative terminology. But the Bible is clear that "each person was judged according to what he had done" (Rev. 20.13). We're left to interpret what those people will be thinking and feeling. But I think that since we will be in the presence of God, our knowledge will be made complete (1 Cor. 13.12). And if our knowledge is made complete, we will find ourselves in agreement with everything God has done, and we won't regard it as a punishment, but as righteous.
> I thought that Jesus took all of our punishment upon Him?
He did (Isa. 53.5-6). NO doubt about it. Those verses particular pertain to atonement that leads to our salvation: Jesus' death on the cross. That's what those verses are teaching. He took our sins and the punishment of death that came with them, and bore those in our place.
> Romans 8.1
What a beautiful verse. Again, this condemnation is the penalty of death for sin. N.T. Wright says, "The condemnation in question is the Adamic condemnation spoken of in 5.12-21, which in turn looks back to the condemnation of sin in 1.18-3.20." We are freely pardoned for the sins of our life by the grace and mercy of God. But look at Romans 8.12-13: "Therefore, brothers and sisters, we have an obligation—but it is not to the flesh, to live according to it. For if you live according to the flesh, you will die; but if by the Spirit you put to death the misdeeds of the body, you will live." In other words, living by the Spirit is not automatic, but we must choose it, by faith and allegiance. And we will be held accountable for what we do with what we have been given. To him who has been given much, much shall be required.