I'm not sure what you mean by "silly folder names" on the stream, sinse the folders all have sensible names, eg, other books, music, podcasts, notes, text, just with a dollar sign in front. The Usb transfer is actually so easy I often do it just for quick things, eg, when I was at aims music school for a week and was given unexpected stuff to do, I stuck specific tracks on my victor to listen to while I was wandering around, a process that probably took less than a minute, indeed that is one instance where a cloud system would've been inconvenient sinse the flats where I was staying didn't have a fast net connection and requested not too much downloading.
It certainly is something that might have it's uses, especially with what you say about note taking and word processing on Ios, but I've largely given up on the idea of an Iphone as a device for listening to any media on. Thenn again if I do go with the mac thing I know there is a lot of compatible transfer stuff between Mac and Ios anyway, indeed my brother regularly uses his Ipad as a note taking device and then transfers directly to the Mac.
One thing I'd also be interested in with Ios 9 is whether web navigation with vo will improve. When my desktop when capput last month i tried to use this forum with my Iphone, but ran into various problems. Some were obvious like the problem of vo really not working with dropdown boxes and how even with the rotor navigation to find headings I was frequently doing a lot of flicking, but some were just plane buggy, for example I actually couldn't post on this forum with my Iphone because for some stupid reason it was impossible to click on the submit button even when I'd written a post, vo just made the click noise and nothing happened (when I rang Apple to talk about the mac, this is one thing we did test and the chap agreed with me it was a bug).
Then again to be perfectly honest I confess my mind just isn't on this sort of thing right now. I'll see what Ios 9 has going, but really it's hard to concentrate on much else besides, ---- well my lady at the moment, indeed one reason the mac thing is not as much an issue is the desk where I was going to put it I might need for her computer if we decide to live together in my flat.
With our dreaming and singing, Ceaseless and sorrowless we! The glory about us clinging Of the glorious futures we see,
Our souls with high music ringing; O men! It must ever be
That we dwell in our dreaming and singing, A little apart from ye. (Arthur O'Shaughnessy 1873.)