Overstaying a visa

Hello,
Firstly, thank you for taking the time in providing these services, they are much appreciated.

I have a problem relating to overstaying my visa. It has now been approximately 10 months since overstaying my visa, I had previously attempted to renew it however I was unaware of the change in law and the increased regulation.

While I acknowledge I should have been more aware of these changes I have several questions in relation to these changes:
1. Will I be allowed back in the country after exiting and paying the fee? I am a student and would like to eventual continue studying here.
2. The reason I was unable to renew my permit was because of a funeral I attended (on the day it was expired) as well as a medical condition that requires me to have an escort which further delayed my attempt to renew to the point that I was told to leave the country in order to renew. Because of this medical condition as well as financial reasons I could not leave the country until now. Will these factors help my situation, should I bring certification of these issues when I leave the country in a few weeks?
3. Will I be detained when leaving the country, or do I only have to pay a fine? Where can I find an accurate quote as to the amount of this fine?
Finally,
4. With the help of a lawyer and the above documentation will I ever have a chance to earn citizenship if I choose to return and stay here in the future? What steps can I take?

Also, I am from the USA, and the visa was a tourist visa (I had temporarily stopped studying).

Thank you very much once again.