Hi and welcome! I don't believe it possible for VA's to pool together to obtain health insurance since VA's are typically self-employed or work as subcontractors for a larger multi-VA firm. You'd have to be an employee of an organization that offered group insurance in order to obtain it that way. Otherwise, it's individual health care. Secondly, yes, I'd highly recommend learning a bit about computer technology - having your files backed up is crucial! There is a plethora of information on this site alone to help you along with that.
About licensing requirements, those vary by state and can probably be easily found online by googling it.

Just dig right on in, and don't be afraid to ask questions!! Good luck with your journey!

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--Leigh