H1B extension and travel before expiry of current visa

[us2011indy]

My H1B visa and I-94 is going to expire on 30th May 2013. I am in process of applying the visa extension but the application is not yet submitted for final processing.

I have to visit India in the month of March for family reasons and will be back to US by 31th March. I will have exactly 2 months left for initiating visa extension process before the visa expires. I am planning to file visa extension soon after coming to US (on 31st March).

Do you see any major issues/concerns while coming back to US at POE for :

1. Only 2 months left on my Visa (and previous I-94)?

2. Will there be concern raised by Officer at POE, why not filled the extension yet?

3. Do you suggest filling extension before leaving US and travel to India, with just Acknowledgement receipt for filing visa extension ( not the approval)

4. If I file extension before leaving US , then will there be any issues while returning(on 31st march) as my extension would already be in process, but surely approval would be pending by then.

Thanks in advance for your reply !!!