I'm a freelance web designer, and have been producing websites since 1999 (I started at 15). I managed to get hold of a copy of Adobe Photoshop 5.5, as released in 1999, along with Dreamweaver 3, Flash 4, Fireworks 3 and a few others of the same vintage. I upgraded DW to version 6 (MX) when someone gave me a copy and a key for it.
I still use PS 5.5 almost weekly as part of my job with one of my clients, and still do a lot of editing in DW MX. I haven't upgraded either because of both the costs involved and the changes to the user interface in both pieces of software in the last 10 to 15 years.