WebkitGTK versions 4.0 is being removed from gentoo's main repo, in favour of the equivalent 4.1 version. This breaks PlaydateSimulator which dynamically loads libwebkit2gtk-4.0.so.37.
The dirty hack would be to symlink the newer sofiles to the old filenames. Any sane person would dislike this approach though, as it specifically works around the package manager and messes with system-wide libraries. Instead, we can patch the ELF to directly request the newer versions.
cd $PLAYDATE_SDK_PATH
cd bin
patchelf --replace-needed libwebkit2gtk-4.0.so.37 libwebkit2gtk-4.1.so PlaydateSimulator
patchelf --replace-needed libjavascriptcoregtk-4.0.so.18 libjavascriptcoregtk-4.1.so PlaydateSimulatorFile names can be adjusted according to what is available on your system and what the current version of the SDK requires (ldd PlaydateSimulator and look for not found entries).