Rambling about Reading

More about reading comprehension: I have a couple of workbooks I use sporadically with D, he really does learn quite well from them. My main concern is that I want to be sure he can USE what he learns. It's a toss-up at times between making him read above his level and improve, or having him read at his level to develop thinking skills. He spends a lot of time re-reading a sentence until he "can think about it and know what it means." Advising him to read the next couple of sentences even before he understood to see if it would be explained further on helped. He couldn't understand on his own that an idea may be introduced and THEN explained. He always leads up to an idea step by step, every detail.

He has a very specific way of thinking I guess. Once I told him, "I think when I learn something new, I put it in my brain and move it around until I find where it fits. I put it there and it's done. It seems you do things a bit differently. I think you get a new bit of information, search for where it fits, then you pull back to look at the whole picture to see what it looks like with the new information. It seems to not make sense to you until you run through everything you know with the new facts or ideas in place." He replied, "Exactly! That's exactly it!" When he's hurried at all, in any way, shape, or form, he can't take that step and the piece floats away - vanishes. How do you speed up someone who needs to do that? Should he be hurried? If allowed to take that step, he remembers and understands, or at least, he's much more likely to do so.

I have a few books like The Greatest Adventures of All Time by Life (Magazine?) that I may have him read. They're compilations of short stories that he can work from without being overwhelmed by an entire book that he didn't choose. I'll also use a recent one out by Time that I'm working on a study guide for. It's science so that will help, but the reading level is way above what he can understand (the author waxes quite poetic at times, D gets really thrown off by that). Good, that gives me time to complete the guide for it.

I just talked to him about his current book, The Fellowship of the Rings, he's understanding it! Of course, he's watched every movie about ten times each, but still, he can read it. It's taken four months. And he just told me he's reading The Silmarillion at the same time! And he understands it! This is great! Letting him have "reading class" in which he can read whatever he wants without any worksheets, summaries, analysis, just reading what he likes, has helped.
Maybe he just has so much trouble with his history book because it's not only difficult for him to read, but he has no framework organized in his brain to fit it in. He loves numbers, says he can understand a sentence if it has a number in it, wouldn't you think dates would work? But the timeline idea failed totally so far.