The link between this and the Gen 6 verses about Sons of God, daughters of men and resultant Nephilim is obvious. One interpretation that I like is that fallen angels were invited by men to demonically posses them. Then these demonically posessed men became "mighty" and other men married their daughters to themm. Thus while angelic beings did not directly marry women, they posessed men who did. Their offspring were not genetically different (some could have been giants, as the Amalekites of Joshua's day, who were also called Nephilim), However, their fathers, demon posessed men, made sure they would be "mighty" in this world to further spread Satanic influence.
This would then mean that God decided to imprison those particular angels that so closely entwined themselves with mankind that they could be said to have "gone after strange flesh." and Jesus preached His own victory over the entire Demonic enterprise as they would be unaware, being locked up in prison rather than roaming the earth as many other demons.
I also do not see a problem with both Jesus and the thief on the cross descending into Hades. If we look at Jesus' parable of Lazarus and the rich man, "Abraham's busom" could have been a place in Hades separated from the true Hell, but not yet Heaven. This would fit well with the Greek perception of "the Elysian Fields" as a Paradise within Hades. It could be that this place was abolished after the resurrection when, Adam's debt being paid, all those souls were taken from this "holding area" within Hades to Heaven. This is not strange considering that Heaven itself is but another "holding area" and not our final destination. As I like shocking people by saying, Heaven is a nice place to visit, but we will not want to live there. Our ultimate destination is a New Earth, specifically the city New-New-Shalom (Jeru-Jeru-Salem) after the resurrection of all FLESH.
Anyway, more stuf to ruminate.
JR