I'm kind of stressing out about this a little bit. I think it's figuring out WHEN to have him memorize the multiplication facts- should I have him do that before we actually start the multipl worksheets? Or should we start on paper (with ones he can count out easily as addition first i.e. 2x2 or 3x3) then, when I'm sure he knows the concept, have him memorize?
Meghan, if I were not using CLE for math (which provides all the introduction and drill needed), I would probably (after teaching skip counting on a 100-chart) draw representations on paper or whiteboard and explain something like this: Here are two dots. If we draw this just once, we have two dots. We can say it as "two dots one time is two dots." Now if we do two dots again, we have two dots two times - now how many? Four, right. Now if we do two dots again, we have two dots three times, or three times two - now how many? Six, right. Here's how we write that: 2x1=2, 2x2=4, 2x3=6. Now you do one. Okay, now let's do three dots. Three dots three times is what? Nine, right. And we write that as 3x3=9. Don Potter has a Multiplication Matrix on his site http://www.donpotter.net/education_pages/math.html (scroll down the page) that you may find helpful, as well as links to "heritage" math books.
I agree with Lindina on how to approach multiplication facts. We use Math-U-See, and they start multiplication by showing blocks (laid side by side like graph paper) for each set of facts with blanks at the end of each row for skip counting. That way they see the concept behind multiplication and the facts stick in their head after skip counting practice. MUS also has online drills where you can practice all the math facts and try to better your time.
look for mulitplication array worksheets. They are great to get the idea across that multiplication is really simplified adding.