My version of Cool Edit 2000 was bought in January of 2000. Paid US $ 69. That’s ~ US $100 in 2018 money.
I think this is the version just prior to CE Pro. Has only 2-track (i.e basic stereo) editing/recording. The help pages (a local copy) say you can buy a plugin to expand that to 4. (Well, not now, of course.)
Anyways, this version works fine on Windows 10.
CEP (v2.x) might be a different beast.
For history buffs:http://homerecording.com/bbs/user-forums-by-brand/cool-edit-pro-adobe-audition-forum/cool-edit-audition-release-history-235201/
That link has a post saying that CE Pro was CE2K with all the plugins included.