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Laidoff: 60 day grace period ending soon. Few questions

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I got laid off July 05 2017 and my 60 days grace period ends 3rd of September. I have couple of questions:

1. What is the latest date I need to find an employer and file for a H1B transfer in order to avoid leaving the country? I assume the LCA takes around 1 week. Can I continue to stay as soon as I apply for LCA or H1b transfer?

2. In case if I decide to overstay 1 or 2 months after the grace period, just to give it a last try or to settle things, what's the worst that could happen? I know couple of my friends did that and had no problems. Some stayed for at least 4-5 months. 
3. If I find an employer after the 60 days grace period and file for H1b transfer, while I am still staying in the country, what kind of problems would there be?
Is there anything else I should know given my situation?
I would appreciate any feedback.
Thank you


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