I am on OPT (exp in Aug 2017). If H1b not picked up in lottery, then I will be applying for COS to H4.How to avoid break in job?


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I am applying for H1b this year. If not picked up in lottery, I will be applying for COS to H4 and H4 EAD together in May. I would be requesting H4 start date to be August 6th, (August 5th is my OPT expiry date), so as to avoid break in my employment. However, most likely via this route, there is going to be a break as current COS processing times are long. 
My question is, in order to avoid break in employment, 
1) Can I apply for H1b and COS to H4 at the same time? As currently there is a lot of delay in COS time, if I apply for COS after H1b rejection in May or June then there might be a long break in my employment. 
However, I am not sure if I can apply for both H1b and COS to H4 at the same time. If the answer is yes to this question, then I would like to know: If my H1B petition gets picked up before COS has taken place, can I withdraw my COS petition? What if, COS happens before H1b gets picked up? What happens in that case? Will my H1b be rejected? 
Please guide what would be the best way in this situation or any other way to avoid break in employment.

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