military school.

Quoting Dragonmamas:

How old is he? To send your child off for being a child is absolutely ridiculous. I call that lazy parenting.

 I don't agree with it but I also have never been a mom of a teen.

Maybe he needs a Whine Jar, similar to a swear jar.  Every time he whines, he has to put in some change.  When it's full, the money goes to charity or maybe towards a present for a sibling.  You don't want to get a present for him with the money, because he'll whine day and night until there's enough for an Xbox in there.  I've never heard of someone who wasn't at least a teenager doing this, though.

If he's younger, he might not be that good at expressing his feelings.  When DD doesn't want to get her boots on, it's usually because she wants to play with a toy that's too big to bring to the store and well, no one likes cleaning much.  I encourage her to say at least "No" and "I don't want to" because people other than me tend to think she's just throwing tantrums for no reason.  Maybe you can ask why he doesn't want to put his boots on instead of why he's crying.  Also, try to get him to clean after every activity.  When he's done with his puzzle, attempt to get him to put away that one puzzle before getting something else out.  Smaller messes are less overwhelming.

How old is he? I think sending him off would only make him more insecure with you.

I agree. Sometimes parenting can be aggravating but you figure out what the problem is and fix it. Not just send him off to have someone else do your job.

Quoting Dragonmamas:

How old is he? To send your child off for being a child is absolutely ridiculous. I call that lazy parenting.

THIS TOTALLY. Or if they are sick.

Quoting abra:

My kids get whiney when I'm not giving them a secure and structured enviornment with boundries and lots of love.