Hi Pappy. You sound like me. An old guy at war with technology. I'm losing this war. Anyway, I'll tell you what I know. Don't worry, it won't take long.
I have an iPod and iTunes loaded on my computer. iTunes is a free download. Any music files you have can be played on iTunes. I plug the iPod into my computer with USB cord, make a playlist on iTunes and the chimps do the rest. I assume this would work with any Mp3 player but don't know for sure.
Hope this has been some help. Good listening.