I came back to college after my OPT. problem applying for working visa?

Hi,

I have been working as a programmer for 2 years using my CPT and OPT. I worked from May-2012 to August 2012 using my first term of CPT. From August 2012 to August 2013, I worked using my OPT. I didn’t win the lottery for H1B last year so I have to come back to school (add another major to my college degree) to maintain my F1 Visa. While in college, I currently working using the last 9 months of my CPT. I will graduate with both degree this May.

Would it be a problem for me when I apply for H-1B this year?

Plus, given that I win the lottery this year if they have one, am I allowed to stay to US from May 2014 to whenever I know the result of my visa application? If I get the approval, am I allowed to stay in the US until Oct, 2014?

Thank you.