I'll answer the first one for you. Simply, if it's important enough to your son, then he should do the asking. If he's not willing to get over the fear (maybe it's not fear but just doesn't want to be seen as complaining or something of that sort) then it's really not a big deal. It's also a great way to learn that even though parents are there to help, they aren't going to hold your hand (once again, I'm not accusing you of this, because you probably just want what's best for your kid, but nothing is keeping an almost grown man from doing the same thing).
I'll let you in on a somewhat weaker time of mine, that I turned in to a positive. Almost my entire high school career I didn't see eye-to-eye with the coaching. Summer coaches were better coaches (with less time) than I truly felt my HS coaches were. Now, that's not to say I didn't think they were smart(I want to stress this, the atmosphere at my HS allowed for mediocrity. We were going to make the playoffs, that's amazing enough right? Wrong.), I knew they were smart. When I individually talked to them about baseball theory, pitching, hitting, etc, knowledge was there... but it wasn't stressed to the kids. I saw it from day one and everyone dismissed me as an arrogant (I can be) freshman, but it kept brewing and boiling until senior year (and it happened in lesser amounts throughout) I lost it. To me it was unacceptable that fundamentals about baseball were not getting through (I felt like I had to do the coaching sometimes) and it was killing us as a team. I had been through it for three years on varsity and had been on teams that could've done things with the right buttons being pushed in practice, in the weight room, etc. I lost in, and exploded. No doubt, coach was ****ed (rightfully so), so I had to explain myself.
I wrote a note/letter almost 6 pages long detailing among other things: my commitment, my previous understanding of how to play the game, flaws and failures directly from the players, flaws and failures from the coaches. I also apologized, offered specific solutions, and decided to offer my uniform if he saw it fit, but I had almost gotten to the point where baseball was mundane (baseball should never be mundane). I read it to almost every senior, and one junior making sure they approved. I reworded things, and added things they felt were important.
When I went in to talk to him, it was hours before a game suspension I had received for the previous incident. Needless to say, I broke down no-more than 5-6 lines into it and struggled through the whole thing. I was fair, I was honest, I was tough on all the coaches and all the players including myself. When it was all done, besides being completely embarrassed (I thought by reading it 10+ times I wouldn't have to worry about that aspect), I tried to immediately leave. He stopped me, told me thank you and that he wished I would've done it a long time ago. From that day on, practice was different--it was more productive. Work outs were different--they were tougher. We worked on the physical and the mental. It worked, and the team noticed and we responded. I believe he's using multiple suggestions of mine now, not because he hadn't thought of them before--I knew he had, but he didn't realize the team wanted that.
My parents were frustrated with the atmosphere at my HS and my gut tells me on multiple occasions considered offering to go do my dirty work, but I had to. I would've had it no other way. I have the utmost respect and confidence in those coaches now. They never lacked the knowledge, but they needed a player's voice.
Obviously, this is not the same as asking about playing time, but a kid's voice means so much more and is often taken with much more sincerity and concern--like I began with, a kid wouldn't be in there unless it was important enough to stick his neck out there for.
I do not mean to insult the coaches from my HS in this post, but sense some inevitably will or could, I will take this down in a few days. I loved my experience in HS, it got exponentially better the day I read that letter.