It may have a lot to do with first impressions. For me, it was a 2000 around 1987. So it boils down to a bit of nostalgia in that respect. I did not have the same attraction to the Pet I used in high school, or the Tandy my friend had, or for that matter, my first PC, a 486. I got a lot of mileage out of the 486, but it was more a tool for college than the discovery of a fun machine.
I came back looking for Amiga around 2004. Now I am interested in it as hobby, a curiosity. It's different from the work PCs I used daily.
