It seems that if Daijisho doesn't recognize the game (even if it shows you every single detail about the game), it won't run it.
This happens with dolphin and RetroArch as well. You can make this be a double press and you can set which tab you want it to. Also, pressing the home button will make it go back to daijisho. For some reason occasionally this gets reset back to Quickstep, just go back and set it back to Daijisho. Daijisho System settings -> Apps & notifications -> Default apps -> Then set the Home app to Daijisho.