Hey Trevor,
there exists a hack that preconfigures the Onefinity Controller to already know the display resolution at boot, so you don’t have to worry to turn on the monitor first. You can find it here, but you need to edit and save a config file inside Controller.
The explanation is, when booting up, the Controller tries to retrieve information from the monitor in order to know its resolution. If the monitor isn’t accessible at that moment (because you switch it on later), the Controller cannot set the monitor’s resolution. The hack above avoids this by setting the resolution in advance, so auto-probing at boot is omitted and resolution is always correct.