You don't actually know anything about the regulations you mentioned...especially FINRA. I dunno what you think you need from Azure that you couldn't get from almost any cloud provider, but you're wrong.

Most major cloud services providers (Azure, Linode, Rackspace, AWS, Google App Engine) have HIPAA compliant data centers and are happy to sign BAAs. FINRA (which is an independent regulatory company...and not actually all that relevant as an example given their purpose) uses AWS themselves. None require a hybrid solution to achieve compliance with HIPAA/HITECH.

As for services like e-mail/365 if you're storing PPI in unprotected clear-text files that can be accessed without any sort of logging/tracking of the accessor you're most likely in violation already. I don't care WHAT you're using for e-mail. In fact, just don't fucking e-mail PPI around. I've had to have that talk with CSRs before.

I'm very sensitive to people expressing things about HIPAA when they don't know what they're on about. Posts like this convince some idiot HR director that he's an expert and knows "Those cloud things don't work for HIPAA" when it is a flat out lie. HIPAA is enough of a mess without the masses getting the wrong ideas.

In fact you'd be very hard pressed to find regulations that can't be met with your standard cloud services, and you'll find excessive amounts of documentation from those providers on how to maintain that compliance.

I can't speak to the rest of your statements (except that yes, Apple products DO suck in an enterprise environment) - but based on your misinformation about regulatory requirements and the cloud, I'm skeptical.