Re: Learning iTunes.
I now have my Stream up and running, and can confirm that there is absolutely no need to use the provided software; you can do it all from the player, with the exceptions being so rare they might as well not qualify (advanced networking settings, podcasts not listed in a public directory). The only thing you will need help for is activating an Audible account, if you have one--but awesomely, once done, you can actually keep your AudibleActivation.sys file in your backups and just stick it in $VRAudible and it works on any SD card. Bloody marvellous!
I know for a fact that using a Stream will make life easier for me, but I also know that I will lose out on some of the convenience of having iTunes do all the work, especially for syncing positions between Mac and phone in podcasts and books. Still, on balance, control is a wonderful thing and if this means I can just carelessly pick up my player and bugger off instead of having to first organise a space shuttle takeoff which is what iTunes sync constitutes, that's great by me.
You can do backups using iCloud; you don't need iTunes for that. iCloud backups however do not include passwords. To be honest I just wipe and reinstall when a new OS release comes out, or at the very least check everything again anyway, so it makes no odds whether or not I have a backup. Time consuming, but once done it's done.
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