Is it possible to transfer music files from a 4th generation iPod to computer?

Some many years ago I loaded nearly 300 music files to a 4th gen iPod from iTunes. That iPod still plays those tunes on itself, as will iTunes on my computer when the iPod is plugged in.

My problem is the files are stored only on that old iPod (not within iTunes / on my computer), and I want a means to either transfer or copy them to my computer in the event the iPod gets lost or becomes inoperable. I have tripped over this problem for some years and give-up every time due to no success. Thinking I once asked an apple CSR (via phone, 1-800 maybe) and the response was basically that it couldn't happen. As part of a renewed effort just today, I struggled through a WikiHow-to How to Copy Music from Your iPod to Your Computer. I downloaded and installed SharePod with little success, finally updated iTunes after years of non-use, and it seems my best efforts are all in vain.

If nothing else works, given the community's anticipated input / responses, might it be possible to remove the iPod's disk and treat it as an external drive? I tend to have personal logic problems these days, but I know my limits... To put it into perspective, imagine how awkward it'd be to replace 289 tracks, downloaded from numerous sources, with a playlist entitled Chronicles of Rock, with songs by name, artist, and release date, from 1965 thru 2006 !!! Yes, it was done with iTunes, but the playlist now exists exclusively on that ancient history 4th generation iPod.

Happy Holidays to All

[Re-Titled By Moderator]