I'm a big Ashton fan. I prize the 2X size, which are perfect for my use.
You mention 1X pipes, they are somewhat rare, so don't mull it over too long before making a decision.
Taylor era Ashton prices have held up fairly well on Ebay, Craig era less so.
I've tried several Craig pipes and found them lacking. BUT, the last time I owned or held one was at the 2016 or so Richmond VA show. Craig has a terrible business plan for marketing his pipes (really, a lack of a plan), which in my opinion, hurts his reputation.
KCGhost mentioned Bill's alcohol problem. It was joked about after his passing, but latter era pipes can have build issues. (early 2000's to 2009) So check those high double-digit year pipes carefully. I think at the end, Craig was making the pipes and Bill had little involvement.
This is a pretty interesting read, at the old PIpeSmokersAlt group, following Bill's passing. (Mark Tinsky and Maxim from Pipes2Smoke going at it!)
groups.google.com