Working backwards from the Model S, I realize I've had quite a few...
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2012 Jamis Coda Sport bicycle. Main motivation was to bike with my kids, but they're not into it yet. Even so, I now ride frequently -- to commute, to exercise, and to escape. Despite a few months off from falling and breaking my leg last October (yeah not fun), I still enjoy biking, and I've gone a total of >1600 miles so far.
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First iPhone (3GS for me). It can be problematic and distracting since I check it all the time, but I love having the entire internet in my pocket, just a swipe and a few taps away. I love this quote (
apparently from Reddit):
I possess a device, in my pocket, that is capable of accessing the entirety of information known to man. I use it to look at pictures of cats and get in arguments with strangers.
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Current house. In parts of the DC area, it can actually make economic sense to buy an old house, tear it down, and build new. A friend of mine did it in 2005, at which point my wife said unequivocally (and I had agreed) we'd never do something so crazy. We signed the contract in mid-2008 and moved in ~1 year later. Like @stevezzzz, I might have been an architect in an alternate universe, so I had a blast customizing the floor plan and making the house energy efficient. I didn't have the foresight at the time to install a 240V outlet in the garage, though! (BTW, earlier this year, my wife also said we'd never be so crazy as to buy a Tesla, and I had agreed!)
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Our twins (born in 2005) -- not a "purchase" of course, but they have certainly been life-changing and have exceeded all expectations!
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2-week honeymoon in Hawaii in 2002. Incredible trip, 3 islands, furthest we've ever traveled from home (so far) and our longest contiguous vacation (so far).
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"C2K" - a Caribbean cruise in 2000 with a group of 30 people. I had started planning it 10 years prior as a way to stay in touch with friends from high school after we all split up for college. The 30 people ended up including many people from college, as well as my then-future wife.
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1996 Acura Integra GS-R 4-door -- my first new car. Slight stretch for a recent grad with student loans. Manual transmission, tons of fun to drive, and it was still running nicely 111K miles later when I had to give it up for the "twinmobile" (2004 Mazda 6 wagon). The Mazda was a good car but doesn't make this list.
* Reaching waaaayyyy back, I could throw in the
Amiga 500 (1989?) and
Commodore 64 (198x?). I first learned programming on the C-64, and that set me on a path to software engineering, which I still enjoy.