Could I get some advice on transferring music files from an old iPod to a newer device? [View all]

I have an old legacy iPod (2006. Sheesh! Old). I have a ton of music on it, and the computer I stored the files on doesn't really work well anymore, and I no longer use it.

Anyway my 16 year-old iPod no longer plays very well on a playback dock (mine is an iHome), and not at all when hooked up to my car stereo.

First of all, it's not my car's software; I already had a tech support person ask me that. My other iPod plays very well in the car. The guy at Ubreakifix said it was likely the input/output-charging port. They could solder on a new one and put in a new battery for around $175.

They also said I could simply transfer the data from the old iPod to a newer one using a large-memory thumb drive. I tried something like that about ten years ago, and all my playlists ended up on the new device in reverse order.

Any idea how to do a simple data transfer? Thank you.