I went from a cheap mp3 player that I could just plug in to my computer and drag in music to an iPod which forced me to download the iTunes bloatware create an account and then took 100x longer to transfer music because of the pointless conversion each file had to undergo. This was my first and last experience with a personal Apple device. Ended up putting some old pop music onto it and giving it to my grandmother after 2 days. Uninstalled iTunes and went back to using my cheap mp3 player until I replaced it with a smartphone.
Coming in as a close second place, an all-in-one Sony Vaoi computer that cost a fortune and had shit performance. Took daily nags to Sony before they took it back and gave me a refund. I find that Sony’s hit and miss though. My favourite smartphone (Xperia Play) was Sony, and I love my Sony Bluetooth earbuds. The Sony Smartwatch was shit.