"You got to walk that lonesome highway / you got to walk it by yourself." There's a whole cluster of folksongs & hymns that take up this theme of the individual confronted by meaningless nature. The solution, rejected by Wittgenstein, is usually some exterior force, a god or an ideology. And this leaves the traveller even more alone.
Christopher Robinson & Joseph Duemer read Wittgenstein's Philosophical Investigations
Just a quick response to your first area of inquiry: Wittgenstein accounts for selfhood and individuality in much the same way. These qualities, always provisional, are the result of our constellation of memberships in language-games. This is a form of perspectivism that may be considered more dynamic than even Nietzsche's. Wittgenstein's account of who we are, who we think we are, and the obstacles we must overcome to arrive at a self-definition is predicated on a peripatetic view of the person. Simply: life is a walk through an occasionally lonesome valley.
All right, glad to see you back. For the moment just a brief response. I've been thinking about two sorts of things recently: 1) The way that what we call the self is a provisional & ongoing process & 2) the way the "personal" works in poetry. Particularly 20th+ century poetry.
The only one of your statements  that gives me any pause at all is the first one & then only because that information about your work with the dying is that it may not be common knowledge among your friends. To someone who does not know you very well, your statement would present problems of verification. Perhaps, in your humility, you don't make this practice of yours public.
As for the others, my wife is the most beautiful woman I have ever seen, but that doesn't mean I won't accept your statement. Both statements can be true. It is delimited by the first person pronoun. Anyone with a wife will know what you mean. (This turns out to be more interesting that I first thought.) In the case of bench pressing, I could, as you say, drag you to the gym & make you prove it, but there is also a common sense objection--you don't look like a weight lifter.
 The remark that inspired Thomas Kuhn (among others). Here Wittgenstein observes the fluidity of propositions, concepts, and definitions. What is the source of this fluidity? It is the character of my knowing. Knowing is provisions. Claims to knowing have different requirements for verification, and verification itself is fluid. Think of how we assess the following claims from me:
1. I saw a man rise from the dead last night
2. My spouse is the most beautiful person I have ever seen.
3. I can bench press five hundred pounds.
On statement one: You might note that I work at Hospice as a volunteer care-giver. I have seen many people resurrected from the dead thanks to the marvels of modern medical technology. It is not a Lazarus-scene, but according to the old definition of death -- the termination of respiration and heart beat -- it is valid.
Statement two: What are you going to do, hook me up to a polygraph? We allow such statements to go unverified. They are no doubt true for one in love.
State three: This is observational. Let's not be too insulting.
This is a long remark, but it could be much longer. We have only offered illustrations of the provisional quality of our claims to knowledge. Even those classified as "scientific."
 Okay, I have struggled with this remark in the past and I continue here. Wittgenstein asks us to think about a comparison between "knowing" and "saying." He offers a series of statements or displays of knowing. Wittgenstein says, for example, that "how many feet high Mount Blanc is" is an illustration of knowing and not being able to say it. But if I knew how high Mount Blanc is, I would be able to say it. "Mount Blanc is this many feet high." There is a difference between this knowing that can be expressed in a statement and the knowing involved in knowing "how a clarinet sounds." This would be an instance of ostensive knowing. If I could identify the sound of a clarinet -- "that is a clarinet!" -- this would verify my claim to know the sound. In the Mount Blanc example, the verification is contained in the claim. Either I have the measurement correctly or I do not. Ah me. This is a hard one.
I did not see your question regarding the relationship between analytic and post-analytic philosophy. You are correct: It did not come about as a result of a synthesis with continental philosophy. Rather, post-analytic philosophy is a consequence of a single book, Richard Rorty's Philosophy and the Mirror of Nature. The book was perceived to be an attack on analytic philosophy by an analytic insider. This is an overstatement. Nevertheless, the effect of this book and the essays Rorty published the following year as Consequences of Pragmatism was to create a huge crack in the foundation of analytic philosophy. Professionally, philosophy remains an analytic game in the US. The three major journals of philosophy are not refereed. Rather, publication is determined by a board composed entirely of analytically trained professors of philosophy.
So how did analytic philosophy become post analytic? It certainly did not come about through the work of continental philosophers. They were mostly ignored and, by and large, were content to explore continental philosophy, rather than engage in criticisms of the mechanistic research programme. Hence the development of the analytic/continental divide. [Philosophy.com]