I gonna have 2.5 months gap next year..My lawyer told me that if I want to stay in this country , I gonna have to get a I-20 from kaplan for summer before my OPT expires..Then i can stay as F1 till the end of first week of september, then as usual I will have 60 days to leave the county or chage my status..So in that case, my H1-b will start from October so I am safe as my visa status will be changed from October first before my "60 day grace period" expires...This is a suggestion given to me by top immigartion lawyer , fees paid by my future employer, ..this has been working for them so it should work with us too..According to him, eventhough your H1b will be void if you go back to F1 after your H1-b is approved but USCIS has accepted the above mentioned practise as an exception to this rule for people who have less than 6 months of "GAP." He even said, USCIS is working to solve this issue , possibly by next year, they will allow people to stay at most for 6 months if their H1B is already approved ... Hope this helps..