🎶 iPod Woes / Android Music Apps and SD Cards — Recommendations Needed

Yesterday, my iPods went south. I don’t mean that they went to Orange County (although one of them did); rather, I mean that they both are not working. Last night, after syncing them to iTunes 12, they both got into endless reboot loops. Given that this happened to both of them, I suspect a Windows Update corrupted the Apple Device Driver. I will attempt to reset them, and may need to reinstall iTunes, but there is the possibility that they are useless until Microsoft fixes the problem.

Le sigh.

So, the question is: What to do to get me back and running. Here are the critical parameters of the problem:

• In my iTunes library, I have over 45,000 songs, and about 100 podcasts, MP3 and AAC format.
• Size-wise, this iTunes library is between 256GB and 512GB.
• I do not want to stream music; I prefer to play it from downloaded copies
• My iPod Classics are my only Apple ecosystem devices. I have a Windows 10 PC, and an LG G6 Android phone.
• I would prefer to be able to use my smart playlists and retain my ratings and play counts.
• My LG G6 does have a MicroSD slot, and I’m open to getting a 512GB MicroSD for my phone.

I see two options at this point, and I’m open to suggestions about which to do. For the sake of this discussions, let’s assume that I get the SD card, install the card, format it, and mounted it.

Option 1: Google Play Music.

👍: Google Play Music has a music manager that runs on Windows 10, and can see and read your iTunes library. It permits you to upload up to 50,000 songs to its cloud library, although if the track is already in its library, it doesn’t upload your copy but uses its local copy. It appears to then permit you to download those songs to the SD card and play them from storage. It contains a podcast feature, but it looks like Google Podcasts may also integrate with the same storage.

👎: Supposedly, Google Play Music will be going away in favor of YouTube Music, but when that will happen is unknown. Supposedly, Google will make the transition seamless. It is also unknown the extent to which Google Play Music supports smart playlists. Playlists may be limited to 1,000 songs.

💲: $9.99/month. $14.99 family. It looks like you can do a free option as well, but the limitations of the free product are unclear.

Option 2: Apple Music,

👍: Apple Music integrates with iTunes on the PC because iTunes is Apple Music on the PC: You just set iTunes to upload to your iCloud account. It permits you to upload 100,000 songs to your cloud library, although if the track is already in its library, it doesn’t upload your copy but uses its local copy. It does not upload tracks it considers to be “poor quality”. It appears to permit you to download those songs to the SD card and play from storage. There is a separate Apple Podcasts app that supposedly integrates. Smart playlists supposedly move over.

👎: First, it is a continuation of the Apple ecosystem. Supposedly, iTunes will be going away and transitioning to the Apple Music model. The impact of this is unknown.

💲: $9.99/month. $14.99 family. There appears to be a 3 month free trial, although the limitations are unclear.

ETA: Option 3: iSyncr + Rocket Player

While researching Apple Music, I ran across a product called iSyncr. This appears to — for a one-time $10 fee — run in the background and sync iTunes information to the SD card on an Android phone. It syncs stats (bidirectionally if you use their player) and ratings, and handles smart playlists by syncing a snapshot of the playlist. As long as it syncs play counts back, that’s fine. They have a music player called Rocket Player that works with their app.  I’d much rather give a mom and pop operation my money on a one-time basis than give the highly-profitable, tax-avoiding Google and Amazon a monthly fee. Right now, I’m leaning towards this option.

Based on my research, it appears that if Windows Update fucked this up and the iPod Classics are dead, I’m going to need to move to a subscription service, about $120/year. That’s the bad part. It does look like I can still keep the music in iTunes and after the time-sink of uploading and downloading, have the music locally on my phone. But which service? Right now, I’m thinking Apple simply because it has a larger song limit and assuredly supports Smart Playlists. Google is appealing to get out of the Apple ecosystem, but (a) it is Google, and (b) it may be going away with the transition unknown.

I’d like to hear your thoughts and experiences.