Re: getting a new iPhone, some help needed, please
Outlook Express an efficient, bloat-free client? Ugh! Never! Outlook Express was essentially a web browser masquerading as an email program--"Client" is too generous a term here, since its only real connection to email is that it (poorly, of course) implemented the email protocols used for sending and receiving messages.
Having said that, if you want an Outlook Express that doesn't suck, you could do worse than to try Thunderbird. It's competent, has a very similar feel, and is extensible so you can turn it from its fairly simple out-of-the-box state into a pretty awesome power-user mailer. I daresay your lady could learn it pretty easily, if that's what you need.
Outlook is a crappy email client, but it makes up for that (to some, small extent) by being a general-purpose personal information manager that also knows how to deal in contacts and calendars and all that. iCloud integration is provided by iCloud for Windows. Set up iCloud on the iPhone first, or you won't be able to sign in on Doze. Requires Win7 or better.
Re file management, as of iOS 9 it's better than it's ever been, and probably it's as good as we're going to get. You can store any type of file, in any directory structure you want. And yes, Apple's own productivity stuff now uses this mechanism. To see what your iCloud Drive looks like, go to Settings, iCloud, iCloud Drive, and turn on the "Show on Home Screen" option. Now, use the app that just magically appeared on your home screen to look at your iCloud Drive file storage. Any other cloud storage provider can hook the exact same pickers in applications, as I said; for Dropbox, for local servers, for privately-managed servers, etc, there will be an app that shows you your stuff and a document provider that exposes that stuff to apps that want to "Browse" it. It's pretty nifty, and really, I think it addresses the worst aspects of the older "Document storage" which was stupidly limited and didn't provide the "File system" that people were clambering for in apps like Dropbox (and especially Dropbox, it seems to me).
Now, if you specifically want to extract audio files from iTunes you’ll have to use iTunes itself to get the files, by syncing them over from your device, or by downloading them from the store. iTunes is what Apple calls a “Shoebox” app, i.e. the data of the app is containerised. So yes, the media folder on a computer is the only way to get the media out. But once you have the media out, you can dump it in your cloud storage drive of choice, as I said, and avoid using iTunes (and the Music app on iPhone) to play them back.
The point of iTunes Match is to allow you to put all your music (that you already own) up in the cloud, so you can get to it from anywhere, so you aren't limited by device storage, so you have Apple’s high-quality rips (if you have inferior-quality alternatives), and so you don't need to sync. If you want my personal opinion, iTunes Match would be made less attractive, even pointless, if iTunes allowed you to download songs to your devices locally from your own home computers on your own network, instead of requiring that they be uploaded to the cloud first before they can be accessed (even offline) from your devices, or else requiring that a sync be manually started from your device to get just the music you want, which you know full well is painful. The flip side though is that with iTunes Match, any number of libraries can be accessed as one--a use case I don't care for--and that Apple is giving you high-quality song files for you to keep as replacements for the crappy ones you may already have. I think iTunes Match is pure profit when you consider that Apple has a strong interest in not providing iTunes users the server capability to download locally--indeed, the capability they do offer, called "Home Sharing", only allows you to stream (but not download) content from your own home computers from iOS devices. Coincidence? Of course not! But it’s the only option there is, so I suggest people with the patience to tag do it. And yeah, most people don’t know how to manage their own home storage equipment or diddle with file and folder structures, and probably don’t keep lossless tracks as I do when they have the chance. It’s hard to argue that Apple isn’t providing what people want (again), just as its competitors are doing.
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