Before proceeding with other questions, it is necessary to define terms. The first is the word, "Hell." There is a bit of a difficulty here because of the translation history of this word. The King James translators translated the Hebrew "sheol," the Greek words, "Hades, Gehenna, and Tartarus" all with the word "Hell."
The old English word, "Hell," was the equivalent of our modern English word, "hole." It could refer to a cavern, pit, or other dark place. Like a clothing merchant who was called a "clothier," a man who patched "hells" in a roof was called a "hellier."
This idea actually carries the idea of several of these words well. But we will start with "Hades."
The word, "hades," had a long history before its use in the New Testament. In classical Greek literature, it usually refers to the underworld as the abode of the dead who lead a shadowy existence in it. It was also used to simply refer to the grave or to death. Greek-speaking Jews used this word for the Hebrew, "sheol," which carries much of the same range of meaning as the Greek "hades." The idea of being buried in a grave (hole in the ground) is probably why the King James translators chose the word, "Hell," for the Greek word, “Hades."
In the New Testament, "hades" is used 10 times (Matt 11:23; 16:18; Luke 10:15; 16:23; Acts 2:27, 31; Rev 1:18; 6:8; 20:13, 14).
Jesus holds the keys to Hades (Rev 1:18), which means that Hades cannot imprison anyone that belongs to Christ. Jesus himself went to Hades, but did not remain there (Acts 2:27, 31). He was triumphant over death and now holds the keys to death and Hades. That is why Jesus says the gates of Hades will not prevail against the church (Matt 16:18). Death and Hades will both be cast into the lake of fire (Rev 20:13-14). The faithful, those whose names are in the book of life are spared from the lake of fire and will be with the Lord for eternity.
The most descriptive picture of Hades is in the parable of the rich man and Lazarus (Luke 10:15). The rich man died, and went away to Hades where he was in torment. In contrast, Lazarus was in "Abraham's bosom," which gives a vivid Ancient Near Eastern picture of honor. Imagine an ancient dining room where everyone is reclining on their left elbow at the table. The place of honor would be to the right of the host, which would place the guest of honor literally at the bosom of the host. At the last supper, John was apparently sitting in this seat of honor (John 13:25). In this parable, Abraham's bosom is a picture of being the guest of honor at a celestial banquet. Lazarus is the guest of honor!
Hades, then, is simply the abode of the dead. The faithful Christian will not be imprisoned in Hades because his Lord has the keys to death and Hades. Hades will be thrown into the lake of fire (Rev 20:14), but the faithful will go on to the New Jerusalem (Rev 21:1ff).