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Is there pushback within the psychiatric community as to it being fake or falsely attributed symptoms of another disorder/disease?

Yes, it's a very controversial diagnosis. Only a small number of psychiatrists, primarily located in the US, are responsible for almost all DID diagnoses. Gillig, 2009 provides a good overview and presents some of the case for not separating it from borderline personality disorder.

"They concluded that DID had “no unique clinical picture, no reliable laboratory tests, could not be successfully delimited from other disorders, had no unique natural history and no familial pattern.”

One of the things that really stood out for me was just how much sensitive, emotional, and personal information these apps can collect.

Isn't that data collection essential to their value proposition? How could an app like Bearable do what users want it to without storing sensitive personal info?

And to be honest, I just don’t trust most of these companies. They seem to care about profit first and protecting their users’ privacy way down the line from that. 

Is that impression based on anything objective? If Happify, for example, were a privacy-first company that prized user privacy far above investor returns, what would that look like to privacy researchers on the outside?

To make those questions a bit more broad, if you were to found a company that made a personal health app that required collection and storage of personal information for its core functionality, what would you do differently to ensure that user privacy is prized above profit? How would privacy researchers be able to tell that that is the case?

It's quite the opposite. Almost all DID diagnoses come from a handful of American psychiatrists (Gillig, 2009).

First line treatment for insomnia is CBT-i (cognitive behavioral therapy for insomnia). In studies, it's far more effective for long term treatment of insomnia than any sleep drug, but you do need to be regimented in adhering to the behaviors you learn. The VA happens to have a great app for teaching CBT-i: https://mobile.va.gov/app/cbt-i-coach

If the app doesn't do it for you, you could try one of the many books that teaches CBT-i or find a therapist that practices it, though there aren't very many of them (hence the prevalence of prescriptions for the inexpensive generic drugs you mentioned).

Thanks for your response. If Happify (for example) were to update their privacy policy with those clearly worded assurances, would those changes alone earn them a positive privacy review?