I started with a Series 1 (The reboot released alongside the Series 2, not the original) and from there I got a used Series 4 in I think 2019. Sold that one and got a Series 5, again used, and since then I've bought and sold different Series 5 watches.
Currently rotate between (mostly) a Titanium Series 5, Ceramic Series 3, and a few different Stainless Steel S5 models. I think my next watch will be a Series 5 Ceramic, should I ever find one that's not super inflated in price.
Maybe in another few years I'll buy a used Series 7 stainless. You don't always need the new shiny thing, and if you never play with the new one, the old one will still feel fast enough.