The assumption in culture today is that if I am happy than God is happy with me. If I am frustrated or thwarted than God is not happy with me.
Philippians 4:9–13 (NAS)
9 The things you have learned and received and heard and seen in me, practice these things, and the God of peace will be with you. 10 But I rejoiced in the Lord greatly, that now at last you have revived your concern for me; indeed, you were concerned before, but you lacked opportunity. 11 Not that I speak from want, for I have learned to be content in whatever circumstances I am. 12 I know how to get along with humble means, and I also know how to live in prosperity; in any and every circumstance I have learned the secret of being filled and going hungry, both of having abundance and suffering need. 13 I can do all things through Him who strengthens me.
Paul understood that God was sovereign, and he came to a point where he was at peace and in submission to God's sovereignty, and care for Paul. Paul was engaged in the calling that Jesus gave him. He new that Jesus would enable him to do whatever Jesus wanted him to do. He rested in the love that he had in Christ. Therefore, problems, thorns, hindrances, sin, lost their power to put a damper on Paul's attitude and perspective. God has given you adequate help, in Christ, to have this same attitude and perspective. The choice is ours what angle we will live from, what attitude/perspective we will allow to color our world.
In addition, I don't see Paul being a jaded or hopeless person. He was content, in peace with his position/lot. He was joyful to serve his Lord, in spite of the difficulty that it brought. Eventually, God even allowed Paul to be martyred (probably beheaded in Rome, under Nero) as the grand exit to his race of life. What a way to go!
I think it was safe to say that God loved Paul & was pleased with him. However, if you looked at his life from an animistic angle, you may think that God hated him. Good thing God is not an animistic type of God! Jesus is our propitiation, through which we can have peace with God & have a sonship/daughtership with him. May we be encouraged by this.