Roadblocks or Language Issues?

We're working on writing. I decided to download a software program called "Kidspiration," which uses graphical organizers to help kids put their thoughts together... found it was a lot of work to do something that's easier to do by hand LOL! But thought I'd try "webbing" as a way to put together a paragraph about a character in a book.

We started with Tom's imaginary friend, Lizard, and that went pretty well. So I moved on to Willy Wonka from Charlie and the Chocolate Factory. I put Mr. Wonka's name in the middle of the web, and asked Tom to tell me three things about the character. Tom has watched the movie a thousand times. He's read the book and answered every readin comprehension question correctly. He told me a pile of things that Mr. Wonka DID, but couldn't come up with a single character trait. After much pushing and shoving, I got three traits -- but there was NO way he could come up with examples of the traits. It was simply asking too much.

I realized that Tom really didn't grasp the concept of a character trait. No one has ever asked him "what is so and so like." We ask "what does so and so DO," "when does he do it," and so on -- but never something as abstract as "what is he like?" Somehow, either he doesn't understand the idea -- or doesn't understand the language I'm using to describe what I'm asking for. I don't exactly know which...

I've decided to step back a bit, and use the organizers to help him write about animals -- something that will be much easier for him. We've also been making a "colonial" loom from cardboard, and he had no trouble coming up with a sequence of steps (though his choice of words, handwriting and grammar are still very young).

Had a similar concept/language problem today with skip counting. Thought I'd use SchoolHouse Rock multiplication videos to help him memorize sequences -- he got teary-eyed! Why? he was very upset that I'd mixed up TV (which is fun) with learning (which is something other than fun?!). Now, he loves educational videos -- but apparently up until now he didn't realize that they had anything to do with the kind of learning you do in school (or even in homeschool!). Wow. I just assumed he knew...

Then we went on to multiplication worksheets. Now, Tom has been able to add for many years, and adding 3 to 42 really is a no-brainer for him. Yet he cannot grasp the idea that skip counting by threes means the same thing as adding three and then three again. Yes, we've done 3+3+3+3, etc. Yes, we've made groups of three. We've made triangles. We've done hands-on 3's counting. We've rearranged cards with multiples of 3, and he's put them in the right order. We've done mazes where you follow the trail of 3's. But when he gets stuck, and I say "just add 3," he looks at me like I'm nuts and has no idea what to do.

Are we hitting real conceptual roadblocks here? Or is this some kind of language issue? Somehow, he is not connecting ideas that he KNOWS with the words to describe those ideas. I'm not sure what the problem is... so am not at all sure how to solve it...