He sounds like my daughter and she's an only child that gets tons of one on one time, but it defiantly can't hurt to spend some alone time with just him. ( All kids thrive off of that) As for the crying and emotional issues, I've seen a lot of kids at 5 and 6 just go off at the drop of a dime. For my daughter I think that it is her learning how to be a big kid, because she goes through phases. She wants the new privileges and challenges, but its scary to grow up more so she will revert for awhile. We work through what is bothering her and give her time and then things get better for awhile. I wish I had any suggestions for the school behaviors. Just keep in good contact with the teachers and give consequences for bad and good behaviors. We use positive rewards for good things as well as consequence for bad things. We just started a penny jar and she loves going out of her way to earn a penny, but she can loose one too if she doesn't stop a negative behavior after one warning. Also you mention how he spent a lot of time with your mom the first 3 years of his life because you had problems. Do NOT let this play into your worries about his behavior now. ( this is the pot calling the kettle black thing) I still find myself blaming myself for whats going on with my daughters behavior now ( I was not myself for a chemical imbalance for the first 3 years of her life) It doesn't help to look back, we can't change it, you just need to go forward. Just be consistent, keep talking and be there for him. Its a hard and horrible phase, I know at times I feel like hitting my head on a brick would be more effective, but it should and has gotten better. Good luck.