This app was mentioned in 17 comments, with an average of 1.12 upvotes
If you're already using iTunes, give iSyncr a try. I've been using iTunes on my Windows desktop for years so already had libraries and playlists setup. Didn't want to recreate in another app/program. Found iSyncr and it works flawlessly. Been using it for a long time.
App Name: isyncr 6.9.12 [premium in-app licemse]
Description: synce music between rocket player and itunes
Playstore Link: https://play.google.com/store/apps/details?id=iTunes.Sync.Android&hl=en\_US&gl=US
Mod Features: should create a fake license or somehow bypass the limit of the app to only sync the first 100 songs. See mobilism for past examples of mods for older versions.
I don't know much about it but isyncr may do the trick. I think it only works with songs that don't have DRM which are itune songs after 2009, or so I've heard.
https://play.google.com/store/apps/details?id=iTunes.Sync.Android
Have you tried the higher-rated itunes sync apps on the play store? this one by JRT (maker or rocket player, a really good music player) seems like it would work.
Unless it's a SSD drive, you probably don't want an external drive hooked up in your car, since it could crash fairly easily.
Not sure the setup you have in mind would work, but I did find this on the google play store. I don't have itunes so I can't test, but it looks like it got favorable reviews.
Sorry, I pasted to the wrong link. I mean the difference between this version and this version.
I use iSyncr to sync playlists and music from iTunes to my Android devices. You require a desktop app, and I think the phone has to be in MTP USB mode before you plug it into your computer to get it to work properly.
Edit:
I've paid for Pro on this, so I no longer have the limitations of the free version which is one playlist at a time and of 100 songs.
iSyncr Homepage: http://www.jrtstudio.com/iSyncr-iTunes-for-Android
iSyncr PlayStore Link: https://play.google.com/store/apps/details?id=iTunes.Sync.Android
I use isyncr to sync music from itunes on my laptop to my android devices
https://play.google.com/store/apps/details?id=iTunes.Sync.Android
Use iSyncr to sync all of your music to your SD card. iSyncr will create a default directory (/syncr/) where it'll sync your playlists, songs, album artwork and more. You can create your own directory if you'd prefer:
http://www.jrtstudio.com/iSyncr/Tutorials/Changing-Folders-to-sync-to
https://play.google.com/store/apps/details?id=iTunes.Sync.Android&hl=en (free version limited to 100 songs per playlist per sync, upgrade to remove limits)
Setup a sync interval to sync regularly to update play counts, ratings and any changes that are made in iTunes.
http://www.jrtstudio.com/iSyncr/Tutorials/iTunes-Sync-Interval
Use Rocket Player to easily reverse sync play counts, ratings and playlist changes made on Android. Other players can also be configured to sync play counts and ratings.
http://www.jrtstudio.com/iSyncr/iSyncr-FAQ-Playcount
I think that addresses all of your concerns. One caveat, iSyncr Desktop on the PC side has not been updated in a long time. It may still feel like you're using software from 2011 =/ Good news is with WiFi, you'll interact from the Android side so you'll only have the desktop client running and won't interact with it much after setup.
Give it a try! DM for help with setup, or email our great support staff!
there's an app for that
https://play.google.com/store/apps/details?id=iTunes.Sync.Android
You also need this app by the same dev.
I use isyncr and it works perfectly. Good support as well. https://play.google.com/store/apps/details?id=iTunes.Sync.Android
Yes it is like Apple Music. But it can do a lot more than iTunes.
for offline music https://play.google.com/store/apps/details?id=iTunes.Sync.Android&hl=en
You might try isyncer.