Ooh, as someone with a Masters in Divinity, let me play!
1. As others here have observed, it ties into the concept of free will. God didn't want us to be mindless robots who would just automatically love Him and always make the right decisions; He wanted us to love Him and make right decisions of our own will, as that would obviously be worth more. A sad downside to that is that many people will use that free will they've been given to not just refuse to love God and follow Him in making right decisions, but will commit truly monstrous and evil acts. While God can at times intervene in our lives in miraculous ways, for Him to do so every time (As Rockhead seems to believe a loving God should) would strip us of our free will by directly preventing us from being able to do anything wrong.
2. As Snuggle Bunny observed, Jesus never once said that following Him would mean a perfectly happy, blissful life without any kind of hardship or danger. In fact, He promised quite the contrary: It would lead to Satan and the unbelieving world hitting us all the harder in various ways. It's why, out of the original twelve Apostles (Including Paul and excluding Judas Iscariot), the only one who WASN'T killed for his faith in Jesus was John son of Zebedee, and he was exiled to an island for the rest of his life. However, Jesus DID promise two things: a) That God would be there to help guide us through it, and b) That it would be well worth it in the end when we get to join Him in Heaven forever.
3. Going through hard and painful times can strengthen people and build character. For instance, I was badly picked on in my teens for having disabilities. It was hard and painful to go through, but it caused me to learn kindness and empathy for those who are similarly picked on and mistreated for being different.
4. With regards to the point Rockhead tried to make about God's plan, here's part of the thing with that: God can take even the most awful experiences and bring immense good from them. Joseph observed and pointed this out in the book of Genesis; He was betrayed and sold into slavery by his own brothers, falsely accused of sexual assault just for having integrity and refusing to let his master's wife seduce him, and thrown into prison for that reason, yet God used that to do much good, as it ultimately put Joseph in a position to help save his family, and all of Egypt, from dying in a famine. For a 20th century example, when black teenager Emmett Till was brutally murdered for flirting with a white woman, God used that and the courage and faith that Till's mother demonstrated to help show the entire world how destructive hate can be, and convince countless Americans (Including then- president JFK) that civil rights was a moral issue rather than just a political one. Such events as those and the recent shootings are horrible now, but the day will come when we will be able to look back on them and see not just God's hand in comforting and strengthening the families of those who died, but how He can take a tragedy and use it to help bring about great good in the long term.
But, hey, I'm applying logic and theological truth to a DUmmy's argument. If he ever read this, he'd undoubtedly just call me a stupid "Fundy," probably with a couple obscenities attached as well, and go right on with his ignorant, closed- minded thinking until the day he dies and comes face to face with the God he openly denied. I would not want to be in his shoes on that day.