We've got your back. With the Tough-O-Meter, you'll know whether to bring extra layers or Swiss army knives as you summit the literary mountain. (10 = Toughest)
(2) Sea Level
Winnie-the-Pooh has two audiences: the kids and the grown-ups. We're gonna say that these stories are pretty easy to understand for the grown-ups, and the kids will definitely enjoy hearing the stories, the voices, and the playful language.
There might be some times when the humor goes over their heads, though, especially for very young children who might not get the jokes about spelling errors. (Some adults miss that, too.) Or they might fail to see that "Crustimony Proceedcake" is not a real thing, since "Customary Procedures" might sound just as ridiculous to them.
But all in all, simple is as simple does.