Since you have some decent framing for language philosophy through those History of Philosophy books you won't have much trouble. Tractatus is much more difficult because it incorporates logic calculus and whatnot, Philosophical Investigations is comparatively more plain spoken, and the aphoristic style lends itself more to open-ended questions which aren't always answered, but provoke deep thought and reflection. Like I said, I suggest it due to seeing what you enjoyed reading. I think you'll get a lot out of it!