Ask Paul: December 11 (Premium)

Happy Friday! In this week’s Ask Paul, we look at locally store music, account sync, Microsoft 365, Outlook.com and Outlook on the Web, and a lot more.
Local music
Cdorf asks:

Have you settled anywhere with your local music collection? I know with Google changing to YouTube they changed the auto-upload feature that was available. I have music that I ripped that isn't available on Spotify (my go to streaming service). I used to use Groove to stream from OneDrive and then Google Music after that. I have been experimenting with different options like Roon, Plex, Synology, etc to come up with a hybrid approach where I can play any of my local music collection or stream. I like Roon but it is ridiculously expensive at 14.99 a month which only gives you the option to stream your own music. Plex is cheaper but isn't as intelligent -- constantly reading incorrect tags in the FLAC files. Synology is just kind of meh.

I don’t really play locally- (or home network-) stored music anymore, but I do have my pre-streaming/ripped MP3 collection on my NAS, and it’s uploaded to iTunes Match (for which I pay $25 per year). I could access that content in a variety of ways---Plex, as you note, and others---but it’s kind of archival at this point.

What I did do years ago was upload all of it to Google Play Music. This was probably unnecessary as most of my collection is available via the services, which I was paying for. Google Play Music, of course, evolved into YouTube Music, and I am using that now. So that music I uploaded is still there, and any music I may want to upload in the future would go there as well.

Regarding uploading to YouTube Music, Google allows non-paying users to upload their music to the service, and they can “play uploaded songs in the background, ad-free and offline - even if you are not currently a YouTube Music Premium subscriber.” Premium subscribers (like myself) “can also cast uploaded content or play it from smart speakers and Sonos.” I recommend giving it a shot. Even if you end up paying for it, it’s just $9.99 per month and that includes ad-free YouTube video playback, which is amazing, plus access to all the music videos on YouTube, also amazing.
Windows 10 account sync
brothernod asks:

Is there an official way to easily migrate users, data and installed applications from an old laptop to a new one? I recently migrated my entire family to new iphones and the experience (where the new phone notices the old one nearby, then pairs and grabs all the stuff) is just shockingly good and I'm struggling to believe Microsoft doesn't have something similar. Recognizing that's giving them too much credit, do you have any suggestions for the easiest way to do this? I always worry about missing something when doing this for friends and family.

This sort of came up on First Ring Daily recently, the notion that Windows 10 has a very vague and limited set of settings that it syncs, and that, because of t...

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