My kids and I decided to make a purchase a couple of years ago from craigslist. It was a bright red Sebring convertible that we fondly called the “vacation”. We couldn’t take a vacation that year, so this was our substitute for it. It wasn’t uncommon to hear, “Mom! Are we taking the vacation?” And my reply was always something like, “Is it raining? If not, of course we are.”
Let me start by saying this was not a well-planned purchase. We had the vacation for about a year and a half, and during that time, we got a lot of use out of it. It was a sad day when we had to end our vacation, but all three of us knew it was the right thing to do. 
We had so much fun in our vacation! Although it didn’t initially cost a lot, the maintenance, repairs and insurance just made the vacation too expensive. The previous owner carefully hid many of the mechanical issues, and I, being in love with the thought of having a convertible, didn’t do my due diligence on this item.
This was our second car, as I would never consider parting with my 15 year old Infiniti. Actually, I had 5 or 6 people that were ready, cash in hand, to buy my Infiniti, but I will own that car to its death. 
I will get 300,000 miles out of it… or more.
I’ve been downsizing everything lately. My housewares, my wardrobe, pretty much everything I own. I never realized how much stress is associated with stuff. Embracing the chaos has a whole new meaning for me. I can embrace the chaos by managing the chaos. Less stuff = more time, more money and more peace. I lost about $1,000 when I sold the vacation, as the A/C compressor went out right before I went to sell it. Not having the vacation and all of it’s associated costs, monetary and otherwise, gave me some peace worth more than what I lost. We have some great memories from our vacation and we’ll always have those to cherish.
Where is your vacation? Is it time to end it?
[side note: I got rid of the vacation before I started the challenge. I realized I will never have a need for two cars.]