How to best use iCloud as cloud storage in daily routine

[exi]

So, here's the thing. I'm an all-Apple household at the moment -- iMac (plus Boot Camped Windows 10 Pro), MacBook Pro, iPad, iPhone, AppleTV.

I treat my iMac as the parent source for all data -- a huge music library, documents, the usual. I backup via Time Machine to a Time Capsule as well as an external HDD via USB 3.0.

All machines and backup destinations are encrypted.

Because I still don't trust iCloud Mail, I use Fastmail for contacts, mail, calendars, and notes. I DO use iCloud for photos, Safari, and Keychain.

When I do use other devices, I often find myself wishing I could just seamlessly access things without having to think about how something is on my iMac and not the laptop, etc. I'm trying to figure out how to best do that when some of the documents in question are things that are at least somewhat sensitive from a financial or other standpoint. Is there is a good, efficient way to do this?

 

[profets]

I've slowly moved to using iCloud for nearly everything except:

-Mail: I use Fastmail as well (custom domain, live syncing of read status)
-Dropbox: I use this for documents/folders for which I share and collaborate on with others

I did spend years managing photos and music collections manually as files on a NAS and other disks, but I've gotten to the point where all of that media is in iCloud. And on my Mac I have iCloud drive enabled for desktop and documents as well. Essentially nothing really sits locally on my work iMac that I can't access from my other devices. It's a pretty freeing feeling. Besides my iMac at work, I use a few iPads at home/work and an iPhone most of the time. I do still have a Mac mini sitting in a basement closet at home that keeps a full local copy of my iCloud Photo library and that gets backed up with Time Machine. It also holds a lot of video based media (older home videos from camcorders and such) that we watch through Plex but are also all backed up.

The big things that I find really convenient for accessing anywhere are files via iCloud Drive, and photos via iCloud Photo Library.

Is there anything specific that you find you wish you could access without thinking about where specifically they're currently residing?

 

[exi]

I used to use Dropbox too -- moved away from it because my need for document and other collaboration is minimal with what I do. Much prefer Fastmail for what you said as well as the power user features as well as me not being worried about the reliability of it as has been discussed with iCloud by myself and others here.

As for iCloud, basically, the thing is that I have a few documents I frequently access (logs, other odds and ends) and occasionally have new things created. What would be nice is if I had a central repository for everything where I could, for instance, access said spreadsheet log and add to it from any device, use my phone with "scanner" type apps to add PDF scans of documents directly, so forth.

My concern is that a few of these documents contain sensitive information I'm hesitant to have in the cloud. Some of it is financial/personal, some "just" personal, some legally protected. I don't know if there's a good way about that other than file-specific encryption.

 

[profets]

I hear you. Honestly I do a lot of that type of stuff - accessing random spreadsheets / logs, saving pdf files and documents. Using iCloud Drive has made it very convenient to just access at anytime from any device.

I do have some financial type of stuff saved in there too. For a long time I never did - just kept it local on one Mac. There is a valid privacy concern, but for myself the convenience outweighed it.

 

[exi]

I think my biggest issue is a combination of the financial data and the legally protected data (think federally -- HIPAA and other laws). With the latter, it's obviously highly regulated, and to the best of my knowledge, Apple has not and is not likely to sign a BAA attesting to iCloud use within the scope of HIPAA.

To be fair, there is only a small handful of files that would apply. Obviously, my home machines contain no other more sensitive data. I presume file-specific encryption in conjunction with iCloud's own encryption (as outlined here) would be reasonable -- so even if some file named "exi-medical-records.pages" somehow was made available to a million people, it would be unreadable, thus no breach has occurred.

As in another thread here, my other issue is going to be a meticulously hand-tagged personal music library which I can't see Apple Music + iCloud Music Library handling 100% properly. Lots of classical music with multiple recordings of the same piece, etc.