Earlier quoted context omitted.
As a counterpoint, Facebook got criticism for each redesign but if they kept their 2001 aesthetic it would look and feel incredibly dated now.
Craig's List looks dated, but remains incredibly functional and is still the top site in its segment. Its dated look doesn't scare people away. It is still very functional. That's the important part.
Meanwhile Facebook marketplace is nipping at their feet while they are staying static.
Clearly Craigslist is incredibly profitable and successful, and possibly more profitable in the short term because they aren’t investing, but IMO remaining static means you lose ground eventually.