Cultural equivalency is an extremely challenging topic. Let me give you a few principles, a few of my conclusions, and then a book or two to follow-up.
The first struggle we have is where in the Bible we should start. If we start with 1 Corinthians 11:3-16 or 1 Timothy 2:12 and then look at other passages in light of these, we will likely have one mind-set as we come to the answers to our questions. If we start with Galatians 3:26-29 or Colossians 3:10, 11 (this passage does not explicitly mention women but taken together with what Paul says in Galatians we can see that the principles are the same) and then look at other passages in light of these, we will likely have another mind-set as we come to the answers to our questions. If we start with how Jesus spoke to the woman at the well (the very first person Jesus clearly tells that he is the Messiah), the woman caught in adultery (look at how he stoops down with her and writes in the earth - this would have been shocking for a Rabbi to get down to the level of a woman and the level of a sinner), or Mary, Martha, and other women whom he regularly discipled (women were the first to receive news of the resurrection - does this book-end the first part of Genesis where Eve is the first to sin?), what conclusions do we make? To me, these latter places (Galatians 3 in particular) are a better place to start rather than with the words of the Bible that deal with problem people in problem churches (such as 1 Corinthians 11 or 1 Timothy 2).
At the end of much study, I have concluded that, in the culture in which we live, Jesus wants women's voices to be heard in the church and in society. I believe that all leadership roles are open to men and women. I am prepared to stand before Jesus at the final judgement and say, "Lord, I have studied and tried to understand Your teaching and I have done my best to teach it to others. If I have erred, I have erred on the side of raising up all people."
For further reading, I would highly recommend the following books. Finally Feminist by John Stackhouse and Christian Perspectives on Gender, Sexuality, and Community by Maxine Hancock (editor).
I will also include a quote from Colossians Remixed (page 211) by Brian J. Walsh and Sylvia C. Keesmaat. In this section of the book, Walsh and Keesmaat relate how a conversation might have happened at Colossae as people read the letter to the Colossians and wrestled with the role of women in the church.
"Phoebe is a deacon in Cenchreae, Junia is a prominent apostle, Priscilla is a woman who teaches and proclaims the gospel equally with (some even think better than) her husband, Aquila, and many other women work hard to proclaim the gospel in their respective places," [Tychicus] said.1
Apphia remained skeptical, remarking that while women in leadership might go over in the larger metropolitan centers such as Rome or Corinth, it's a different story here in the Lycus Valley. But she trailed off as she realized that she was speaking to Nympha, not only a successful textile merchant but the leader of a house church in Laodicea, just ten miles from Colossae.
Tychicus added that he had heard the formulation "There is no longer Greek and Jew, circumcised and uncircumcised, barbarian, Scythian, slave and free also include "There is no longer male and female."2
Nympha pursued the point. "It's clear that Paul is undermining the structure of the household in the empire, especially in relation to slaves. We need to listen clearly to his words, for when he suggests that slaves be freed, he does so in the context of the whole household system by also mentioning both women and children. My fellow believers, you know that when we became part of this Christian community, we gave up these allegiances. You know that we all became part of a new household, which does not support the hierarchical economic structures of the empire but in which all exist for the benefit and mutual service of others. You all experienced the coming of the Spirit, promised to both old and young, sons and daughters, slaves and free. You know how Paul's teachings have challenged the very basis of our society by contradicting the emperor's edicts on compulsory marriage, by urging widows to remain single, by urging us all to choose a life free of the encumbrances of marriage.3 It is no surprise then that Paul is also challenging the basis of the paterfamilias, which the empire regards as fundamental and which we have replaced with a new household in Christ Jesus our Lord."
As she paused, the older Jewish brother slowly got to his feet. "Our sister is right," he said. "We should not let our fear of the emperor keep us from following the call of our brother Paul to end these worldly structures. We have suffered for this gospel before. It may be that we will suffer again. But we are subject to Jesus, not Caesar. And we are citizens of the kingdom of the beloved Son, not the empire.
"We now need to spend some time in prayer, so that we may wisely discern . . .
I hope all of this is helpful. Please don't hesitate to ask me questions about it or challenge my thinking in this area. We are all learning together.
1 Romans 16:1-12; Acts 18:26; Philippians 4:3; Colossians 3:15.
2 Galatians 3:28.
3 In the Leges luliae "widowers and divorcees of both sexes were expected to remarry after a period of one month. Widows at first were expected to remarry after a one year period, but, following protests, that period was extended to three years" (Schussler Fiorenza, "Praxis of Coequal Discipleship," p. 233). Cr. 1 Corinthians 7; Paul Zanker, The Power of Images in the Age of Augustus (Ann Arbor: University of Michigan Press, 1990), p. 157.