Kalopani,

I don't think it would be a much hassle to get work permit renewed when you already have one. You just go through International director to apply for the renewal. They will approve it. However, you have to apply 2/3 months in advance.

You also can apply for OPT. If you do not fall under STEM degree, make sure that you OPT remains valid until next September. I think now you don't even have to worry about the gap if your H1 is approved.

Good luck, Kalopani.