My family has been car free since July and so far we are really enjoying the benefits and are getting used to the costs. I'm new to the sans car forum so I'll tell the story from the start.
We (wife and I) had been tired of being broke and wanted a change in lifestyle. I won't get into politics, but I made a commitment to somehow find a way to live without a car. We were currently living in Phoenix with long commutes and being without a car isn't much of an option when you have 2 small kids. Phoenix has many great qualities but it is not very bike friendly in my view. Before we moved, I had been riding 56 miles round trip (3 times a week) and when the temps hit 100+, I wasn't able to keep up the pace...time to move.
We are both teachers and decided to leave the country for several reasons. Where we chose to live was influenced heavily by cycling. We found jobs working in Holland...arguably one of the best cycling homes. I guess I'm saying that the most important thing when getting rid of the car is to live somewhere that you can operate without one. What does that mean? The place must have a good network of bike trails. What about groceries, buying big things, and getting to a late night party? Use the subways, trams, trains, when and where you can. But let's talk about your bike.
You need an all-weather bike (fenders, etc.) with water proof bags to hold what you need for everyday runs. We have bike seats on the back of each bike and a 2-seater trailer that doubles as weatherproof cruiser for the kids, or cargo space for medium loads. Have big purchases delivered. It's also a good idea to have another bike as a backup in case your commuter is inoperable and you can't repair and get to work on time. You also need raingear for different seasons.
Before I moved, I was just a on again off again bike commuter. Now it has become a lifestyle. It has been an easy transition because of the move. I am not concerned about being hit because dedicated bikes lanes are great here in Rotterdam (NL). The shopping is always close by because this is a biking culture. We'll see what happens when the dark, cold, windy winter arrives.