Aaron,
Sorry for the trouble!
Can you please try this build of 2.2.4? It is not the same as the publicly released version: http://local-by-flywheel-flywheel.netdna-ssl.com/support/test-builds/local-by-flywheel-2-2-4-build-2-mac.zip
If the issue persists even after using this test build, please try running the following command in Terminal. Provide the output in your reply here once it’s done running.
"Applications/Local by Flywheel.app/Contents/Resources/extraResources/virtual-machine/vendor/docker/osx/docker-machine" -D start local-by-flywheel