I still use my classic iPod. I'm amazed the thing still works. I expected the hard disk to fail long ago. I had to replace the battery twice, but that's only a few dollars nowadays.
I still use my classic 5th gen with Wolfson DAC daily - it's plugged into my car. My hard drive did fail and I found a guy on eBay that took out my hard drive and replaced with 500gb ssd card. All lossless, all the time. It's awesome and extremely light too.