You should speak with the international student coordinator at the college--they provide good advice and have inside knowledge of the acceptance process and its length.
If you file for extension of B, then change-of-status to F, it will be risky ... but probably not in the way you were thinking.
Yes, you need to show you have non-immigrant intent .... which may be difficult given your frequent 'visits' to the US.
But, the bigger problem will be that they may take a long a long time to process the B extension ... not making it possible for you to get the F in time for school in the fall.
Is there anything else you're not telling us? Possible boyfriend/girlfriend? Family member that has the potential to sponsor you for a greencard?
All of this must be taken into consideration.
Meeting with an immigration attorney would be a wise thing to do.
PROFESSOR OF IMMIGRATION LAW for over 10 years -- This blog posting is offered for informational purposes only. It does not constitute an attorney-client relationship. Also, keep in mind that this is an INTERNET BLOG. You should not rely on anything you read here to make decisions which impact on your life. Meet with an attorney, via Skype, or in person, to obtain competent personal and professional guidance.
You should be admitted to a program that is flexible to allow you to enroll as soon as your B2 status expired in April. Approval of your application to change status from B-2 to F-1 is a requirement prior to being alloed to enroll in the program. Be warned that any form of misrepresentation will have an adverse effect on any future applications for immigration benefit. As such, you must consult with an immigration lawyer.
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