Common problem? Anybody else a little wordy?

Making the word count used to be hard. Ah, the good days. When I didn't get enough from my interviews and I didn't (apparently) understand the concept of researching, I had little problem making the word count that was set for me.
   600 words? Sure. Why not? I'll try it.
   800, okay. Not bad. I can probably do it. I'm a wordy person in general.
   You see some articles in the paper that are miles long, you know? And you just wonder, how the hell do they talk about stuff for that long?
   Well, I don't know, I guess I musta figured it out because here I am, writing another 1000+ word story for TNH.
 
    I know.

    Conciseness has never been my strong point. I listen to audio recordings of my interviews, and I wonder if I really say um that much. But clearly I do.
    So I try to be concise in my articles. Cool, I think I'm doing an okay job. Everything could use a little improvement, right?

    But the conciseness of the information still evades me like hand grasping at wind!

    There are so many questions I realized I need to know about journalism. So many. I want to know why we didn't go over more in class. I think the writing exercises help, I really do. But then you've got time going by and instead of learning how-to, I'm only learning to do. Just write.
   So here are some things I want to know. Mkay?

+ To what extent do I explain quotes? Do I always need to open and close them? How stupid do I assume my readers are?

+ When I've got a story that's well over 1000 words already, do I go back and throw in some detailed descriptions? Is it okay to say that Tim showed up to our most prestigious interview in sweatpants? Is it okay to talk about the gold cross that hangs around Chris White's neck when the story bears no relation to religion?

+ How can I tell what an issue story is? Around this riveting city, the issues aren't many, and when they do pop up, another writer is already writing it by the time I've thought of the idea.

Those are my questions. I want to get some straight answers so that next time I write, I can feel like I did it right.