I figured that taking away my ability to drive will force me to ride my bicycle and make creating the habit easier
Having lived among humans for 40+ years, I can tell you that they cannot trick themselves into changing habits. Fat people buy treadmills everyday...and end up hanging clothes on them. Poor people buy Dave Ramsey books everyday...and use them as paper weights. People just don't trick themselves into doing things. With that said, I hope it works for you, but don't rely on this "trick" to work for you. To bike to work you must ultimately want to bike to work.
I disagree with this assessment.
Here's the thing - in order to work and be paid you need to go to work. If the car isn't an option because its been sold, then what are your other options? Bike. Treadmills and books aren't your only option. You could watch a nice TV show or mess around on the internet instead. But to get to work? It's not optional, and if your only option is a bike, that's what you'll do.
Regarding the questions - how's it for hills? If there aren't too many, I'd get a three speed or eight speed internal gear hub. And definitely fenders. And a rain cape for wet days. And make sure you have lights (if you get really serious, dynamo lights are awesome for commuting).
Regarding hair - wrap it up in something and wear that under the helmet.
Make sure you can carry stuff - either panniers or a big basket on front or both (I like both). That way if you have to run errands, you have space to do so.
Challenges: actively snowing. Do you have an alternative like if it's really bad you can get a ride or Uber or bus? That's my one hang up. Here in the midwest I have this issue about once or twice a year, so no big deal. Also, if you're dealing with ice often get some studded tires and leave them on all winter.