Marriage and process questions

[walkoffshot 0]

Currently on OPT... my girlfriend and I have chosen to take the path of least resistance and get married. We decided this instead of the stress of finding sponsor through employer, which is possible but there is a lot of headache involved.

I plan to hire a lawyer to help with the process but I have a few questions...

1. While on OPT.. I have 90 days to gain employment. I am hoping this will happen but assuming I don't within the 90 day limit and we choose to have a courthouse wedding based on that how much time should we give ourselves so that I remain in status? I understand that once I apply for AOS that I am in the clear but do I have a window after the 90 days has expired or should we plan this weeks to a month in advance? My fear is that if I am on day 85 (for example) and we go get married that I will not have enough time to receive my marriage certificate and send the application in.. which I believe can take a week or several weeks. I want to avoid this if possible.

2. Lets say that I do not gain employment within 90 days and we get married and send in the application, am I still able to gain employment after the 90 days with our application in (pending EAD)?? Or is my OPT void regardless of my AOS and EAD pending?

3. If my 90 day limit is reached, how much time do I really have (ie is there a window period) that I have to leave the country? I know I would be out of status based on my unemployment and USCIS states that it may affect my future F-1 status in the future, but will it affect my application or give me issues during the interview for AOS?

Basically, I am looking for the most pain-free way of doing this. I cant help but say that this has been an awfully difficult, time consuming and stressful journey. Being someone who has went to school in the US for 8 years, obtaining a Masters degree in the health field with a title that is in high demand and paying close to 150K in tuition... it is hard to comprehend that there are no better options. BTW, my degree/title does not match any of the STEM extension programs.. go figure :/... I wish there was a way to have it added... I digress.

Thanks for the help!