1. He claims to not to want to be understood too quickly. If you believe that, you might say he's forcing the reader (or emerging psychoanalyst) to not just take his ideas as a simple list of facts to be memorized. He often rants about other fields being reductive in the face of necessary nuance. You might also justify this by saying precisely that perspective is necessary in psychoanalysis, with the human mind (particularly the suffering one) in all its unexplored complexity being its target. I'm of two minds on this: I see his point, but there are certainly times when such is an obstacle. Of course, that's if you believe him in the first place. He also said he was something of the master, and his audience the acolytes. He was trying to build a new school under his system, after all.
2. Lacan's ideas are indeed complex and extremely tightly interconnected (or polyvalent, as he likes to say). The graph of Lacanian thought has a lot of nodes (ideas), and an extremely high number of edges (relationships between ideas) per node, and thus very high graph density. If you think about it from that perspective, how does one present such a oeuvre in the linear form like essays or speeches? Further complexifying things is that he was building this in situ, his Seminars being akin to live-blogging that development. He often asks his audience if there's an expert on a particular topic and if so, to let him know about some detail. He never wrote a comprehensive final form of Lacanian thought, so any secondary texts you read will be that author's interpretation. All this creates quite the conundrum for anyone getting started.
If you want condensed info and clarity, go for a secondary source (Bruce Fink being my favorite), while noting the above. I'd also say that, like Hegel, Lacan has something of a language of his own, one you can learn. If you find his ideas compelling (I do, and have benefited from them in my personal life greatly) you should still read him as a primary source. Even if you do the actual learning via other sources, I'd assert that Lacan is one of the last of the true Renaissance men, pulling in ideas from everywhere and everywhen, and I also find reading him an expanding experience just from that perspective.
I appreciate the mention of Bruce Fink, as his name is new to me. Any works of his or others you might recommend to me would be duly noted.
Here was my early Lacan workflow: Lots of Freud essays (you need to know Freud's major ideas cold), The Cambridge Introduction to Jacques Lacan by McGowan, The Lacanian Subject by Fink, Seminar VII, Seminar XI.
I've read a lot of other stuff since then, but this path into Lacan worked for me. By the time you've read these, you'll know where to go next on your own. You'll also know pretty early in it whether Lacan is for you. Also, if you don't like Freud (and I don't mean disagree with him, but dislike the overall approach), you can safely stop there.