First windows model widely available in the UK. Died within 3 months, replacement died barely 6 months later, didn’t buy another one till the iPod Nano.
I’d had quite a few mp3 players before it but the 3rd Gen definitely oozed quality, pity the audio and build quality were a bit ropey for me and the few other people I knew with one at the time.
As for first iTunes purchase, still haven’t made one. Vinyl transfers or rips of cds are still my preferred legal method of putting music on my devices.