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The military is even getting on board with "Soft Copies". I got tagged for random inspection coming on base one day at my last base and didn't have my insurance. I showed them the PDF file from USAA and they weren't good with it because they "Couldn't verify I hadn't forged it". So I asked the SF troop for his email address, emailed it to him, had him print it, then he said I was gtg and let me on base...so many things to be said here...

Fast forward, my current base actually has it written in to their policy that soft copies are just as good as hard copies for insurance (Maybe even registration for states that require you carry that...but I'm Oklahoma resident so iffy on that since we don't have to carry it).

As far as security of documents "on" your phone...a few thoughts:

1.) Keep them in a cloud storage utility (Google Drive, DropBox, etc) so that it can be easily accessed and updated from multiple devices. You can select to "Pin" or "Keep a Local Copy" in most of these programs to ensure that you have access to it even if you don't have service.

2.) Android, starting with Lollipop, and the current version of iOS encrypt storage by default. As long as you have a strong password an attacker is not going to gain access to the data on your phone. For the exceptionally paranoid, Android encrypts with your screen unlock password. You can actually root your phone and manually change the encryption password with cryptfs to something different and more complex and it will use that for the initial unlock at powerup but subsequent screen unlocks can be done with a softer password. Trusted bluetooth pairing is a godsend too when it comes to the hassle of entering a password each time.

3.) The bigger thing that worries me about soft copies: Handing the LEO my phone...my unlocked phone. Not that I have anything on the phone I'm concerned about but you never know what an overzealous individual might do or "find" (After downloading...) to create reasonable suspicion for a search or detainment. I carry hard copies and the soft copy as a backup. I'd rather take the hit for failure to show insurance or DL than hand some unknown dude my phone. Most cities you can just fax them a copy later and they tear up the ticket. Making a Xerox of all this stuff and sticking it in the glovebox of each vehicle as a backup is probably a much better last ditch option that doesn't create additional risk.

Sidenote: Tell your buddy that goes to China to take a burner phone/laptop/etc that isn't linked to any of his real accounts and don't put anything on it he wouldn't willingly hand to the Chinese government. Don't connect said phone to any trusted devices/networks on his return. Same goes for any other near peer countries.