How Does H-1 Visa Quota System Work?

I am an Indian and have been living in London for the last 6 years and currently in the process of getting British Citizenship, which I am hoping to get by April and subsequently British Passport by June. I work for a leading international bank in London.
My girlfriend is currently doing Masters in Illinois, USA, so, I am looking to move to US, but understand the H-1B visa is a bit complicated.
My question is, how does the quota system work for H-1-B visa and when does the new quota start, and what's the best period to apply for one? So, If I am looking to move there in October 2015, when do I have to get an employer to apply for H-1B for me (provided an employer agrees to sponsor me)? or, is there a particularly good time to apply for H-1B visa?
Also, is it easier to get the visa if I am there physically in the US or it doesn't matter?

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ANSWER: 

See clip from Attorney Rajiv S. Khanna's conference call video that addresses this question.  

https://www.youtube.com/watch?v=baprYGs8IzQ&t=138

FAQ Transcript:

Well you don’t have any time to lose. Apply right away. The way it works is your H-1 application must reach the USCIS on April 1st no earlier and usually no later. Sometimes they give us three to four days but normally April 1st is the day the quota opens and that’s pretty much the quota closes as well and there are usually more applications received by the government than they have visas almost two to one ratio maybe more sometimes and then there is a lottery held and if you get selected in the lottery then your H-1B gets approved. You go for a visa stamping and you can enter USA no earlier than 10 days before October 1st when your H-1B visa period starts.

What is this thing about October 1st?

The US government fiscal year begins on October 1st so all the quotas including green card and H-1’s they get reset on October 1st.  H-1 you can apply six months ahead of the start date  which is April 1st  so that’s why you file on April 1st  and you begin working on October 1st  but you can enter USA ten days ahead of October 1st.

Nonimmigrant Visas: 
Unless the context shows otherwise, all answers here were provided by Rajiv and were compiled and reported by our editorial team from comments and blog on immigration.com

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