F-1 Visa to Green card issues?

I have been a serious student on an F-1 visa for the pass 3 and half years until a semester to graduation that my dad;the sole sponsor of my education here in the US died.My education came to an abrupt end and couldnt pay my tuition when i had just a semester more to graduate.To cut things short i dropped from school and have been out of school for 6 months now.My serious girlfriend,an american born whom we have been seriously dating for almost 4 years now want us to get married.(We are genuinely in love and not any sham relationship),but my biggest fear is that i may be denied permanent residency when i file for change of status and would be most likely separated from my sweetheart(maybe deported).So my questions are as follow ; 1) Is it a serious issue to have my f1 status changed to LPR if i have been out of status for 6 months? 2) Am i likely to be deported if the change of status doesnt go through?(dont want to be separated from my woman) 3) How bright or dim is my chance of getting LPR? 4) Is it true USCIS toughens procedures for out of status f1 students? 5)Is it true its much easier for a B1/B2 out of status person to get LPR than an out of status F-1 student?. 6) Is it necessary to take an immigration lawyer in my case and what major role is that lawyer going to play if i am to take one? I would be very much happy to have all my grievances answered by an immigration fellow.Thanks