Overstaying on a visitor visa

I am from the US on a 60-day extendable visa, and when I went to extend I was denied for not having my paperwork in order. Now, I’ve overstayed and was told that within the first 10 days of overstay they fine $1K. A couple questions:

What happens if I overstay my visa up to 30 days?
Over 30 days?
Can I process a work permit while here on an overstay or will I need to leave and stay somewhere while the work permit stuff is being processed?
Is there a website where I can find answers to these questions, other than here?
Oh, and finally, I overstayed on my initial landing permit, then got this extendable visitor visa, and now overstayed that. Will they deny me a new visa if I leave the country to get one?

I know I seem like a total idiot. Just let me say that when I initially came, I had a job/apt/work permit promise all set up, so I thought I’d save the money and just come without a visa. After arriving and working a couple of weeks the school tried to make me sign a contract in which I would pay $50,000 as a deposit, and after I refused I found out that they hadn’t began the work permit process for me, and so I had to make the visa run. When I came back I found out that they replaced me while I was gone. Now I’m at another school but they don’t offer ARC, which was fine with me because I was planning on going home in a couple of months. Thought I could just use the 60-day extendable. Got my visa in Macau and the guy didn’t mention that I’d need to show paperwork EVERY time I extended my visa(why don’t people ever explain things here?), so that’s why I didn’t prepare anything. Now I’ve really screwed myself and I’m trying to decide to stay or get a new visa (if possible) or just go home now. I just need to know the cost of each decision. Thanks!

If I were in your position I would just pay the fine and either go home or find a more foreigner-friendly country to live in.