I’ve owned several Sansas (and similar) and they’ve all died on me eventually. I’d guess the USB connect/disconnect was the cause of all of them dying, but it’s been a long time.
I have friends who carry old-school iPods, but my music hard drive is significantly bigger (storage-wise) than the biggest of the iPods, and as a result I have never wrapped my head around what I’d store on a large-storage portable player and what I wouldn’t, and how I’d manage the difference.
I use my iPod Touch as a portable music player on occasion, just storing a handful of things I want to focus on at a given time when I’m out and about. (I’d like to just use my Android phone for this purpose, but it seems incapable of reading music-file metadata correctly.)
My issue isn’t my phone. It’s how I use it. When it’s a music player (Bandcamp, SoundCloud, Google Play Music, YouTube) and a book and a typewriter, it’s great. When it’s keeping the pulse of an anxious world, trying to be my best friend, and nagging me about things that aren’t actually all that important, then it’s the devil in my pocket.