1. Let's say your I-94 was not expiring for five or six months no doubt you could lay claim on the 60 day grace period and get another extension or change of status filed during that time. If you do anything during that 60 day period unless the grace period is denied for any other violation of status you are considered to be applying within the status.
2. As long as the difference between the last day of the 60 days and the period your F-1 begins is not more than 30 days you should be ok. More
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