Are there any philosophers who might be considered affiliated or belonging to the same turn or school, or perhaps hold the same kind of views, as Wittgenstein?
Even though his style is rather simple and direct, Wittgenstein is not someone whose writing you can just pick up and 'dive into.' I'd recommend familiarizing yourself with a lot of context before even beginning to read - not only as far as the content is concerned but also as far as the dialectical form. The Investigations for instance make little sense unless you take care to separate the three interlocutors in the text - separated by single, double or no quotation marks. Similarly, you need to be aware of the separate, stand-alone arguments that litter the Tractatus - that is the only way to give the text structure (the numbering of the propositions creates the illusion of a single strain of thought, pursued to completion, but that's not at all how one should read the Tractatus (if, that is, one wants to avoid frustration).) So, in summary, read a lot of exegeses and/or introductory essays (e.g. Anscombe or Potter for the Tractatus, the Routledge volume for the Investigations etc.) before engaging with the texts, make sure you are familiar with the structure and, finally, a lot of historical context won't do any harm, although that is advice true of any text, philosophical or otherwise.
Now on the other hand, to answer your actual question, are there any other philosophers who write more clearly on the issues Wittgenstein himself was concerned with? I don't know - clarity is certainly a matter of taste. I for one think Wittgenstein is by far the clearest philosopher I have ever read and find a lot of the analytic philosophers that succeeded him and who wrote in the name of 'clarity and rigour' much harder to penetrate. I will suppose that you are interested in (what is now labelled) the philosophy of language. The problem is no-one has written like Wittgenstein or about the things Wittgenstein wrote about in much the same way - and I am guessing you are not after scholarly appraisals or purely exegetical works. The only contemporary philosopher I would recommend in that vein is Richard Rorty - he is a great writer and very lucid and, in my opinion, holds ideas that Wittgenstein would surely have sympathized with.
As far as contemporaries of Wittgenstein, who are usually thought to be in the ordinary-language school, I'd suggest Ryle, Strawson, and Hare. Austin and Searle began to move away from "meaning as use" philosophy, but are considered to be affiliated with Witt (but I do remember reading that Austin called Wittgenstein, "a charlatan").
Although Grice, Quine, Davidson, and Kirpke are not of the same school as W., they are often regarded as the offspring of the Ordinary Language School--though, perhaps, antagonistic offspring.
As Chuck mentioned above, Richard Rorty would also perhaps be considered of the same "turn" as Witt. Kuhn is also a Wittgensteinian of sorts (and Rorty claimed that Kuhn was one of the great heroes of his Philosophy and the Mirror of Nature). And, with Kuhn, you might want to look at Feyerabend (who was also greatly influenced by Witt).
Off the top of my head, I don't know of any philosophers who write with more clarity than Wittgenstein. The Philosophical Investigations are a serious of thought experiments which, unlike most philosophical texts, do not rely on extensive knowledge of previous philosophers.
Is there something particular you are having trouble understanding? I have yet to find a section of the PI that did not yield to a slow, patient reading. And I think that Wittgenstein's style in the PI is directly tied to the content; he is attempting to say obliquely that which cannot be said any other way.
Perhaps you could post a specific question about some passage that is confusing you?
As for the Tractatus, it is much more compressed; however, there is a large secondary literature explicating the arguments and filling in the gaps.