Hi

I worked in San Jose, CA from Dec06-Nov08 under a new H1B visa that expires in 2010. In mid-Nov 08, I lost my job. I was told since my I-94 then expires on Sep 10, my status wasn't Unlawful Entry. I filed to change status from H1 to B visa, cleared all my stuffs, and left US on Jan 09. Overall, I overstayed 2 months.

I have been employed in Indonesia since Mar 09 and my petition to change status was turned down. I wish to to apply for a new B visa to visit my girlfriend in the US. My questions are:
1) Does my H1 overstay record make it difficult to get a B visa? If so, what do you recommend I do during the application and interview for the visa?
2) On an unrelated note, if in the future I get another H1B job, do I have to go through the lottery/subject to new annual cap again?