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Very good question.I myself am in a similar position )) Sharing my own experience, I can say the following: first of all, you need to read biographical books. Wittgenstein was an extremely interesting person. And, what is very important, a very special type of thinker, for whom his own life (work, communication, etc.) was part of philosophizing and a measure of the truth of the developed ideas. Therefore, for understanding Wittgenstein, his biography gives a lot. Russian researcher Rudnev studies Wittgenstein's biography in detail. There is a very informative analysis of his stay in the USSR from several authors at once. The book Wittgenstein: Man and Thinker, edited by the same Rudnev, contains several biographical sketches, of which the most interesting is an essay by the American philosopher William Bartley. There, for example, you can find a detailed analysis of his work in a rural school and the significance of this period for further work as a philosopher. There is even something like a book about Wiegenstein for children – Armenio. “Wittgenstein's Rhinoceros”. I really like this book. But, of course, reading all this will make a little sense if you stop trying to study the philosopher's works themselves. Yes, his main works are very difficult to understand, and I can only boast of understanding individual thoughts and fragments. But there are also notes devoted to other issues: religion, classical music, and the history of Austrian culture. They are completely understandable and give a lot to understand the personality and nature of Wittgenstein's thinking. And, of course, through the logical-philosophical texts, too, you need to wade, albeit slowly, but still expanding the circle of what is understood. You spend a lot of time, but the pleasure is indescribable.
In such matters, much depends on the nature of the questioner's interest — both in the figure of Wittgenstein and in the field itself as a whole, no matter how you define it. It is impossible to have any serious conversation without reading the sources, and it is rather not true that avoiding “complexity” in favor of secondary literature will contribute to anything. But for a naked taste sensation, it may not hurt.
A good overview article in the Stanford Online Encyclopedia gives you an idea of the top positions (stanford.edu English), there is also a bibliography of English-language books from and about Wittgenstein. M. S. Kozlova's article “Ludwig Wittgenstein” in the first book of the collection “Philosophers of the Twentieth Century” edited by A. M. Rutkevich is available in Russian. Another introductory material is audio lectures by Alexander Gryaznov, which can be found on YouTube.
The next level of engagement is what is published as Lectures and Conversations on Aesthetics, Psychology, and Religion: a compilation of Wittgenstein's lecture notes compiled by three of his students. The topics covered in it are not so often heard in the context of conversations where Wittgenstein's surname is used “by the way”, and not in the center of discussion, and therefore reading “Lectures” will act more as a step aside and another introduction-however, valuable.
And finally, the main primary sources, first of all “Philosophical Studies” and ” Treatise…”. Most books on philosophy may seem difficult at first-and not at first — but there is still nowhere to run; it should be so. A philosophical work is not only and not so much a collection of poorly presented theses as a certain mode of thinking, which-with due effort-can be reconstructed in the reader's mind. Taking on an author without the willingness to dive for it with your head is, in my opinion, an occupation devoid of any meaning.