Did Jesus literally mean we should hate our family to follow Him?

Lu 14:25-26 ¶ And there went great multitudes with him: and he turned, and said unto them, (26) If any man come to me, and hate not his father, and mother, and wife, and children, and brethren, and sisters, yea, and his own life also, he cannot be my disciple.

When we look at Scripture, we must look at the Scripture literally.  However literally means that we look not only at the words of a single verse, but in the context of the surrounding passage and the context of the event.  Here, Jesus is speaking to those who are following Him, seeking to become a part of the small group of disciples.  At this point, the disciples had not all been persecuted, but the persecution was coming.  It would not be long before the apostles would all be martyred.  Jesus is not looking for people who will join up with Him for a season.  Rather, Jesus is looking for people who will be willing to stand with Him through whatever may come.  When Jesus spoke these words, He knew that the full force of persecution would come from the Roman Empire (and later, the Roman church).  He knew that those who associated with Him would be boiled, crucified, stoned or exiled.  Knowing this, Jesus did not want people to follow Him who were not willing to make such a sacrifice.  To show this point, Jesus gives a few other examples:

Lu 14:27 And whosoever doth not bear his cross, and come after me, cannot be my disciple.

Did Jesus intend for everyone who followed Him to literally be crucified? Did the Lord expect every Christian for all time to end up being nailed to a cross?  No.  Each of us has a different cross to bear we all face different trials as a Christian.  These trials become our crosses.  These trials are the things that prove to the world we are Christians.  By overcoming these trials, as Christ overcame death and the grave, we show the world around us that Christ in us is more powerful than whatever the trial may be.  If we are not willing to face that trial, we cannot be called a Christian.

Lu 14:28-30 For which of you, intending to build a tower, sitteth not down first, and counteth the cost, whether he have sufficient to finish it? (29) Lest haply, after he hath laid the foundation, and is not able to finish it, all that behold it begin to mock him, (30) Saying, This man began to build, and was not able to finish.

Again, Jesus is asking a leading question.  Here, He is asking who would start to build a building without figuring out how much it would cost.  Jesus adds that anyone who starts a building project without first figuring the cost may end up running out of money.  Jesus is saying that the project may end up costing more than expected and you may end up laying a foundation, and then running out of money and being mocked for the incomplete structure.

Lu 14:31-32 Or what king, going to make war against another king, sitteth not down first, and consulteth whether he be able with ten thousand to meet him that cometh against him with twenty thousand? (32) Or else, while the other is yet a great way off, he sendeth an ambassage, and desireth conditions of peace.

Another example Jesus gives is a king who goes off to war.  The king expects to be able to win the war with ten thousand soldiers.  When he meets an enemy force of twenty thousand soldiers, and the king sends an ambassador seeking peace.  Again, it is a case where the king did not count the entire cost of going to war and he ended up in defeat. 

Lu 14:33 So likewise, whosoever he be of you that forsaketh not all that he hath, he cannot be my disciple.

Jesus concludes this by comparing all of these to becoming a disciple by saying that one who wants to be a disciple, or in our day, a Christian, must be willing to sacrifice all that he has.  This does not mean that we need to burn everything we own and immediately turn against our family, but we must be willing to put Christ ahead of all these things and people.  For example, there are people in some parts of the world who, when they accept Christ as their Saviour, are disowned.  Their family forces them to choose between Christ and the family.  Obviously, Christ is the right answer. Even today, people in some countries are jailed, beaten, their homes destroyed, etc. if they announce that they are Christians.  Does this mean that they should not turn to Christ? No.  Does this mean that these new Christians should not share their faith in Christ?  Of course not.  Does it mean that they may be persecuted for what they believe?  Yes, it does.  As a Christian, persecution is a very real possibility.  Even in the United States, the land of Freedom, there is some slight persecution of Christians.   
In this passage, Jesus is making the point that following Him will be a sacrifice.  That anyone who chooses to follow Him must realize that there may a high cost for making this choice.

Though there may appear to be a high cost here on earth, there is a far higher cost for those who choose not to follow Christ.  Those who reject Christ face a penalty of eternity in hell, an eternity of separation from God as well as an eternity of perpetual burning. 

John 3:16-19 For God so loved the world, that he gave his only begotten Son, that whosoever believeth in him should not perish, but have everlasting life. (17) For God sent not his Son into the world to condemn the world; but that the world through him might be saved. (18) He that believeth on him is not condemned: but he that believeth not is condemned already, because he hath not believed in the name of the only begotten Son of God. (19) And this is the condemnation, that light is come into the world, and men loved darkness rather than light, because their deeds were evil.

In the passage above, verse 16 shows the love of God in that He was willing to die on the cross to pay for our sins.  The passage goes on to show us that salvation is a free choice.  That those who have not chosen a saving faith in Christ are already condemned.  No matter who you are, if you have not chosen to follow Christ, despite the consequences, you will face a greater consequence.  You are condemned to death and Hell.  However, by choosing to follow Christ, you can escape this penalty.  Yes, you may face persecution for a time here on earth, but that will be far better than an eternity of torment in Hell.