[Serious] Generally speaking, is philosophy a worthwhile subject of study?

[John 6IX Breezy]

So pretty much the only way I think I can make things more concise is either to find that elusive perfect sentence that covers all its bases in the shortest/simplest possible form, which granted is always very satisfying if you do find one, or just to be less anticipatory in the first place... which is difficult if you're one, like me, with a tendency to overthink/dwell on things.

That's an interesting observation. I do think the solution is to shift your thinking from an anticipatory position to a conversational one.

By anticipating a question you end up having a conversation alone instead of allowing others to be inserted into it. (Which really only happens in writing; it's harder to anticipate a face-to-face conversation.)

This also means you run the risk of biasing your questions, answering ones that serve your position, and avoiding ones that don't. So perhaps realizing that your best thinking can only emerge in response to other minds, can reduce the need for anticipation, and welcome objections more.