Does Jesus want us to be happy and content? And the correct answer to this depends on your perception of happy and content.
If I look at the life of Jesus, and specifically ask, "Did he want his disciples to be happy and content?" I would have to look at how he treated them. Let's see, he called them away from their comfort zones, took them away from the vocation that they knew, traveled a lot, didn't directly answer their questions, told them things like they must pick up their crosses, called Peter Satan...should I go on?
Yet, he spent time with them,he showed them mighty miracles, gave this same Peter keys to the kingdom...totally confused yet?
Here is my perception: Jesus was not so much concerned with their comfort as he was with their understanding of what it meant to be a disciple. He was honest with them,he loved them, he was okay with letting them struggle. He was very desirous that they grow. He was preparing them for a great mission. Had he sugar coated the reality, that would not have been love. Yet he wanted them to be joyous. He wanted them to know God and find their strength in Him.
As a disciple, should I expect any less? Or the tougher question, should I pursue anything less? Jesus wants me to be filled with joy, but not the joy that is based on circumstance. Rather, he desires that I find the unspeakable joy of knowing God as my Father. The Bible says that Jesus endured the cross for the joy that was set before him. (He 12:2) Some think that that refers to the joy he found in providing salvation for you and I. I think it was the joy he found in being obedient to his Father.
My son, 10 years old, is allowed some reading time each day in class. The other day, he brought a book to me and asked if he could read it at school. It was Radical by David Platt. The smile on his face when I told him yes was ear to ear. Is it because my son loves Dr. Platt? No, it was the joy he found in pleasing his father. That is the joy I want. That is the happiness that Jesus wants me to find.