回複：H1B Cap!!!what am i going to

One of my co-worker ever had the same problem like it, her OPT expired at this May 30th, and she got H1b started from Oct, so during this period, she couldn't work. She stayed in US until July (after Opt expired you still could stay for two months), and went back to Philippine. Now she came back to work.
Since you said your boss support you, you could now use your OPT work till next Feb, and hope your boss do not mind that you cannot work from Feb to October, remind him to sponsor your H1 next year, if he agree to keep the position for you for 8 months, then you do not have to worry about anything.