Why not set a time that you need to leave by in order to not be late. If you get up late or out the door late & won't be able to make it to work on time, then you ride the short route & ride the longer route after work. If her concern is you being late to work, eliminate that variable. The lighting will work itself out with a headlamp/tail light combo & if she's right about the headwind, you may revert to her solution after a few days/weeks anyways.