These are very valid questions which used to perplex me quite a bit.
One thing that helped me to understand how it all works is the book, Trustful Surrender to Divine Providence. You can buy the book or you can read it online in PDF at:
divinemercy.tv/St.%20Claude%20de%20la%20Columbiere%20on%20Divine%20Providence.pdf
It’s not too long, for a book.
Father Corapi explains that we are the clay and God is the sculpter. If we remain soft and pliable in God’s hands, things will go better. Otherwise, He will have to get out the chisel!
Whatever happens, God has ordained it so that we can spend less time in Purgatory and more time with Him. We have to think of things in the eternal perspective, because this is not our home. We are just visiting here for a little while, and our happiness here is only temporary. The more important matter is our eternal happiness. That is why our holiness is more important than our perceived happiness.
The “Health and Wealth” gospel is one of the most widely spread heresies in America. I had been taught that if you accept Jesus as your Lord and Savior, He will answer all of your prayers and you will be happy and successful and well. This type of faith is missing a key component: THE CROSS
Jesus didn’t say that if we follow Him, we are to indulge ourselves, pick up our pillows and follow Him. He said that we must deny ourselves, pick up our cross and follow Him. All of the apostles were slaughtered except for John who was boiled in oil. (I guess Christianity ain’t for wimps!)
If Jesus asked for “This cup to pass” and God denied His request for the greater good, shouldn’t we expect the same for ourselves. Ultimately, Jesus said, “But Thy Will be Done,” and thank goodness He did or there would be no hope for our salvation!
It’s like when I tell my little one not to go out into the street because it’s dangerous, but he can’t understand because he doesn’t “see” any cars. He has to trust that I know what is best for him.
Another thing that helped me was something Father Pinto teaches. You write down all of your memories under one of three categories: Joyful Mysteries, Sorrowful Mysteries, and Glorius Mysteries.
Every life has all three. Then you write next to each of your Sorrowful Mysteries how that event helped you in the long run. He says that our Sorrowful Mysteries are stepping stones and learning tools, but that we often get “stuck” seeing only their negative aspects.
This helped me to see that abuse I suffered as a child made me a better Mom than I would have ever been. Also, I thought my kids were so wonderful because of my doing, but God allowed me to become so sick the last couple years, that I couldn’t perform my duties. I have been humbled to see them become successful by the Grace of God, without me!

My pride in my success could keep me from entering Heaven. My prayer would be to avoid these miseries, but God knew what was best for me.
This project taught me the real meaning of the Scripture:
And we know that to them that love God, all things work together unto good, to such as, according to his purpose, are called to be saints. Romans 8:28 (Douay-Rheims)
Sorry this is so long!

May God bless you and give you the answers you need.
And may Thy Will, (not my will) Be Done!
In Christ,
Lucy