I have opposite experiences! Multiple Linux laptop, with multiple docking stations: a bit of xrandr magic and everything works, forever. (BTW, try setting manually the refresh rate at different values for the two monitors via xrandr, I have solves a similar problem to yours in the past by creating a dedicated display class.)
On a Mac, it’s impossible, I have to plug one cable directly in the computer to make it work, and the quality of the output on 2k monitor is way worse since they disabled sub-pixel rendering or some stuff.
Windows also works decently on this regard, until it doesn’t (my partner’s PC stopped recognizing HDMI monitor at some point, and the debugging was frustrating as hell).
PlexSheep@infosec.pub 10 hours ago
Depends on the hardware I suppose. My Dell dock just works.