You have the High Sierra OS on your Mac. Unfortunately, the emulator does not work with High Sierra. MIT has been trying for a long time to get it to respond properly. Apple made some changes that make it incredibly difficult to get the emulator to work with High Sierra. MIT still have no solution. That explains the issue on High Sierra.
W.r.t. your other beast (I have a friendly Microsoft Win 10 PC) I expect you may not have done a Hard Reset before attempting to use the emulator and may not have updated the emulator to Companion 2.46. A guess, I am not a Mac person. You say "whenever I try to get the Emulator to "connect with code". " ... you should not be doing that using the emulator, you should Connect > Emulator (at least that is how it is done with a PC).