Unfortunately the Ipod is now considered old tech and things have moved on to other ways of consuming music.
I too was an Ipod classic user, bought bluetooth transmitters etc but had to move on from the classic as i realised it was now old school.
One very easy way is set up a spotify account, spend a few nights creating playlists and adding in your songs etc, if you are only using for car it will give you most of your music. Spotify is free and if you like it and work with it you can also subscribe to remove ads and random selections appearing.
or
use Apple Car Play, switch from Itunes to Apple Music and it will match the majority of your music library into Apple music which is cloud based as far as i know and wont involve many files on the phone.
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