Is it harder than I'm imagining in big jets, or in specific aircraft due to peculiarities of their handling characteristics?
Aircraft with swept, low wings exhibit dutch roll worse than other types (e.g. airliners). It's also worse at high speeds and high altitudes.
Yaw dampers vary based on aircraft and flight regime to "attenuating somewhat that annoying-bouncing-back-and-forth-feeling in the back of an airliner during cruise (imagine how bad it would be without active damping!)" to "preventing an oscillation from building in 2-3 cycles to a point where it will cause structural failure".
Thanks for all your input in this discussion. I find both flight in general and the case of the 737 MAX fascinating. Previously the implementation of MCAS sounded absolutely insane to me, but I can mostly understand how they got there after reading your comments.
Many airplanes require functional (electronic) yaw damping to be safe in various flight conditions, because of dutch roll. There are also e.g. electronic control feel systems in some aircraft that must be operational to exceed certain speeds and/or altitudes and not be excessively vulnerable to PIO, etc.