I think you go with what's right for DS right now. If he was in school, he wouldn't be expected to memorize the tables at this age right? I say let him go with the calculator and circle back to memorizing the tables later. Maybe this memorization is a developmental thing, he may not be ready for it. I do think they should be memorizing it later, because multiplication applies to so much higher level math.
When I was a kid we had a family friend who had one of those cheezy casio calculator watches. But he was a C.P.A. with his own business and very talented at math. I asked him why he needed a calculator if he was such a math genius( I was a very charming child smile ) He was so nice about it though, he told me most math professionals wouldn't consistently do math calculations in their head, because accuracy was too important.
Who knows, had he not said that maybe I never would have considered a career in investments because at that age I had "math anxiety."

Incog