Oh my, you do have quite a handful there! It sounds like he's talking his way out of doing things - does he do that with other tasks not related to learning? Just like anything else, it's a habit that's being built and it sounds like he's being rewarded for this type of behavior by not having to do it? I'm just spitballing here, but maybe some type of disciplinary action if he's doing this on a regular basis. You obviously have to be careful with that, but I'd probably do something that made it clear he won't get his way by bickering with authority figures. Of course, you don't want to entirely squash that type of thinking, it can be a good thing when done respectfully, but questioning everything all the time ... a bit much.

I just used a moving company called A1 Auto Transport that has a lot of moving tips, checklists and the like available on their site. It sounds like you're going with the do it yourself method, but some of the stuff there should still be helpful as far as packing, preparation, and planning. Moving is never particularly enjoyable, but it's much easier when you have a plan and keep everything organized. Good luck!

Is he doing any sort of outlining or organizing of his thoughts or just going straight off the top? In my experience, even many advanced students can struggle with their writing, even as far as high school. Part of me wonders if random topics are the best approach - you'll have to do that some of course - but maybe a topic he knows something about would help him to understand how to string the thoughts together better.

So long as there's also reasonable expectation of some struggle and difficulty in being able to do it. Like CuriousMomof3 said, it's a difficult skill, but it's also one that should be cultivated and developed early on.

He's still young. Give him some time to explore his options and take a few classes. Many people change their direction from when they start college to when they finish and tons of people have a career in something other than what their degree is in.

Having formal lessons is really the best place to start with any instrument. You can find videos and other things online but you'll pick up some bad/lazy habits you'll just have to correct later. Get the basics down first.