I have been reflecting along the same lines for a while, here are few thoughts, if anyone is interested.
Philosophy is constructed from two words and could be translated literarily from Greek as: love of knowledge. This implies a "lover", and from this individuality in the act I see flowing a lot of the problems you describe.
From my understanding, Wittgenstein main point is: "meaning is usage". This is a generalization that is a centrality of philosophy itself; Russell alludes to it in "the problems with philosophy" as he sets the reader on a quest to right something that can't be.
Here's my reasoning: since no two person can use a word in exactly the same way, the inherent imprecision of language and of philosophy as a construction is a feature not a bug, a v.useful one still; ever had this epiphany moment of having a great idea because you misunderstood someone?
If you set off to generalize enough on practical philosophy, I guess you get to the wisdom expressed in sayings and in illustrations; they convey by high bandwidth a particular pattern of analysis from one individual to another one that seeks wisdom, but one would be hard pressed to call receiving (as in "idee recues") sayings as a philosophical endeavor.
The way I now see philosophy is it's a quest to a personal worldview acquired through a personal love for knowledge. It cannot be exact nor absolutely true unless you're a dictator or a cult leader. This is why the idea and "ideators" are so closely associated; people talk about A.Rand because through her constructed world view she gives an ethic that have seducing finalities; however as you point out, objectivism as she conceived it cannot be perceived again by a human being let alone brought to new heights.
I find that reading inherently imprecise philosophical material can give very strong insights exactly because of the words are soft, and impact each unique individual in a different way. The ones that are not purposefully unreadable that is (Foucault?), in this I agree with you. "I", as my existing uniquely individual self, personally agree with you; another unique entity that defines itself as an ensemble of cells and electric currents. Seriously, I find it rather unconvincing that because you cannot pinpoint self, or soul, you negate something as evident as individuality, from which "I" choses to defines itself. I guess this fits "l'air du temps", ref Dawkins, Pinker and co. It has the smell of groupthink tho.
(BTW, evilmonkey your comment got me ROTFL)