Hk Kriston,
So glad that you are sharing your concerns. Here's how I've been thinking about things lately:
1) The bottleneck! Less profound than an outright LD, many of our kids have challenge areas that make it really difficult to teach them at their readiness level in their strengths.
2) Spiky Profiles! another way of saying the same thing - theoretically homeschooling is great for accomidating this sort of thing, but IRL it takes lots of trial and error to find the right approach, and maturity on the part of the parent to not blame the kid. Great to hear that you are getting better and better able to notice 'where he is.'
3)Math Facts are important, and Drill is about the only way to do it, although I would throw in neumonics and teach about them as a seperate non-Math class. I'd call it memorization. I'd do a full explore on what he wants to memorize, and which methods he wants to try first. I would also consider allowing him to do this while being emotionally distracted, perhaps by watching an unrelated TV Documentary, or playing a computer game. Or let him test you - have you noticed that the easiest way to memorize something is when you are quizing someone else.
For 'real math' you can let him use a calculator, perhaps making the rule that he can only use it for single digit operations, and has to 'take notes' on what he has gotten from the calculator. Also there are great tables for the facts that he can use to quickly look up the facts while using them in more complicated work. Just write 1 to 9 across the top and down the left side of the page, and allow thim to work on filling out one for addition, one for subtraction, one for multiplication and one for division. Using them over and over may help them 'seep in.' Has he read "The Number Devil?" Anyway the trick is to seperate math into two subjects, and teach each at their readiness level.
For what it's worth, I think that there are some skills that a kid just isn't going to learn before they are developmentally ready. My DS11 had Zero interest in learning to read an analoug clock in Kindy, but was happy to learn at school in first. ((shrug)) It just didn't look that difficult to me, considering the other stuff he was doing.
I think that the basic recipie for self-esteem when dealing with a spiky profile kid is this:
2x as much energy, time and resource on providing for their strengths as for working on the weaknesses.
Don't allow the weaknesses to limit the advanced work or to be left behind.
A little bit can go a long way.
Keep an eye on your mood and on your child's mood.
In other words, just what you are doing!
Smiles,
Grinity