I enjoyed reading your history. Welcome to LCF.I'm somewhere between prospective and car-lite.
I tried biking to work a few times at 17 - 18. I was amazed at how easy it was to cover distances by bike, even in the rural towns I grew up in. I tried to continue cycling in college, but my bike's destruction by vandals in 2006 put a stop to this. I didn't have money for a new bike at the time (though I did find cash for my $450/year university parking permit, and cash to buy a car for $7,500 in 2007). I wasn't to bike again until 2011.
Last summer, I bought another hybrid bike. I rode around exploring our parks and greenway trails. As winter moved in, my pleasant cycling evenings were cut short. To maximize my use of daylight, I decided to try biking to work. I first rode to work in September. In November and December, my old 2002 car started experiencing multiple issues with the fuel pump and factory security sensors. I was left stranded several times, lost the use of my car for about 2 complete weeks, and ultimately had to spend over $1,000 in parts, labor and towing fees. This taught me about the local bus system and carpooling, and strengthened my resolve to commute by bike.
Today, I bike to work between 1 - 3 days per week. I've purchased a Dutch-style city bike.. I have dyno lights that allow me to bike after dark.. I own 2 large grocery panniers that can help me transport even a 30-pack of beer home.. and I own some simple winter gear that keeps me comfortable in temps down to about 15F.. I own an Ortlieb briefcase.. I slowly but surely am adding to my rain gear, and should have a complete set soon.
I still use my car, but often for frivolous or unnecessary reasons. Sometimes I oversleep. Sometimes it's raining, and I'm not ready 1.5hours before work in order to catch the bus. Last month, I had to take my computer in for repair.. and had to drive it 0.25 miles since the tower didn't fit in a grocery pannier.
I'm hopeful that with continued smart investment in my gear, improving weather and the advice I read here, I'll be ready to lose the car the next time it has mechanical problems.