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ANSWER: If you are out of status for 10 days, you are out of status and cannot change your status to H1B on October 1. If you apply for H4 and then withdraw it, it will catch up with you and it would be as if it was never filed. Therefore, at some point in time, it would be discovered that the subsequent change to H1B was never validated because you would not have had an approved petition to bridge you over the 10 days.
One option you would have in this situation is to leave the US and get a visa, and then come back to the US in H1B status. The only other option is to apply for a change of status, get the approval, and then apply for change of status to H1B. But you would not be eligible to start on H1B unless and until the change of status is approved, and the validity date is current.
Aside from that, there is no other way to accomplish this. Unfortunately, the strategy you are considering is not going to work.
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