Why is it easier for some to understand Shakespeare while for others it's much tougher, if not impossible altogether? My first thoughts are pretty simplistic-- they don't concentrate/focus while they read it, etc. But my actual guess is that they don't read it long enough before they give up. I'm not talking about reading with a class because you have to, I mean reading it to yourself and reading for at least an hour with focus, before deciding you can't understand it.
For me, I think it was a combination of all of the simple things above but mostly that last idea; I didn't want to give up. I hadn't read much Shakespeare at all when I arrived a freshman in college, and I felt horribly behind as an English major. So, I took myself to the college library when I had breaks in homework, and I read. Usually right there in the stacks on the floor, one tragedy after another, a comedy here and there to break things up. The weird thing is, the words that I'd never heard of before began to make sense after sort of skipping over them at first, but only when I'd been reading for a good bit.
Of course, the biggest reason is context, and you have to read for a while before that context can take shape and allow you to begin to interpret the old English in the text. Soon, you're filling in the blanks, and that beautiful rhythm helps you along too. Maybe it's the high school English teacher in me, but I think anyone can read it with a little dedication, focus, and time.
It has been a very long time since I've read any of his plays, but I'm thinking it may be time to give the Bard another go.