I have a whole fleet of professional grade Swedish chainsaws, not one of them have I bought new. Most are 10 years old or older. My newest is a jonsered 2260 which I like very much.
Sometimes I get tired of fixing them up and just want to cut wood and those days I consider buying a brand new one.
I have never bought a new saw for myself. I did go to the store and purchase Dad's Husky 50 with his money around 1988. Traded a little poulan, SXLAO Homy + $100. Side note, I've never purchased a lawn mower for myself, always hand me downs and garage sale stuff.
I've never purchased a new saw but still have a Stihl 026 by dad bought new so I could cut up a large fallen tree. (hey, it was bigger than the Skill 1616 we were trying to do it with). I've purchased over 150 used ones though.
Of course I don't have them all, you think there's something wrong with me?