I'm not reading all 4 pages. Just adding in some thoughts from my experience with my 2 boys (one now in college, other in HS).
The Pushing vs Encouraging thing is a fine line. I really tried hard to not cross it. My oldest was more gifted/skilled in baseball, and he liked playing it, but didn't "love it". So we never did travel ball, but did do Rec-leagues which did give him the chance to play in some all-star tournaments that we all enjoyed (state runner-up for 11-12 yr olds, and state champs in 13-14 yr olds). I believed the time commitment for travel teams would quickly burn him out and make him hate it.
I got a Small-Ball pitching machine. That was fine for him to use with friends. But when just me and him, I would hand pitch the Small-Balls to him (you can't replace the timing factor of seeing the ball coming out of the hand). I would even do this with his middle school team (10 pitches each) before games, and they hit better in games when we did that. Hitting that 1.6" ball leads to hitting the center of a full-size (2.9") ball. That's also what my dad did with me 40-45 years ago, although was homemade balls of tape wrapped toilet paper.
When he was younger, coaching his coach-pitch team, I would get down on my knees to pitch to them to get a better age appropriate angle and throw to them with more speed than most coaches. They can learn to hit the speed better than they can learn to hit a pitch dropping significantly. Also there was a rule after 3 swings-&-misses they were to hit off a tee. My team did not. I would instead soft toss to them in that situation, which was something we also did in practices. Had the best hitting team at that age-group by far. Also at that age (6-8) you got to make it fun. So I would do competitive games as drills. Like relay throws, charging grounders & coming up throwing, low pop-up find & catch competitions, or 4 vs 4 vs 4 scrimmages (learned a few of these at Durham Bulls camp I took my son to). Actually the 4 vs 4 vs 4 is a good way to scrimmage with any age group, where 2 of the 3 teams are in the field and the other one is batting until either 3 or 6 outs.
I later assisted with my other son's next age group team, and his coach did not want the pitchers pitching to the batters in practice. Too many balls (not strikes), too many swings and misses, too much standing around. So he'd have us coaches pitching to the kids (luckily I pitched my whole life, so I did 90% of it for his team), and he had the 2 kids on deck and in-the-hole hitting soft toss or off tee into the fence. In that league most teams would average maybe 1 hit to every 3 strikeouts, but our team was the opposite about 3 hits per every 1 strikeout.