I went through a similar process to buy my first car (although I wasn’t considering children relevant, I did consider a dog and skiing supplies, as well as wanting to be able to transport friends). I eventually settled on a $10k used car from a dealership. I was originally expecting to buy a very used $3k car, but was convinced to increase my budget by the idea that driving a maintenance-needing car would be stressful, as you note. Advice I received was that $10k was around the sweet spot for a car that could still go a long time without needing much maintenance. I ended up buying from a dealership, which I considered a worthwhile premium because I knew nothing about cars.
I also wanted 4wd/awd for New England weather driving (I wouldn’t consider this essential for boston, but driving to outdoorsy things in the winter is less stressful with this feature). Also wanted decent highway mileage, mainly for environmental reasons. I ended up getting a 7-year-old Subaru Outback with just over 100k miles on it. It’s been a year now and I’m reasonably happy with the purchase.
I went through a similar process to buy my first car (although I wasn’t considering children relevant, I did consider a dog and skiing supplies, as well as wanting to be able to transport friends). I eventually settled on a $10k used car from a dealership. I was originally expecting to buy a very used $3k car, but was convinced to increase my budget by the idea that driving a maintenance-needing car would be stressful, as you note. Advice I received was that $10k was around the sweet spot for a car that could still go a long time without needing much maintenance. I ended up buying from a dealership, which I considered a worthwhile premium because I knew nothing about cars.
I also wanted 4wd/awd for New England weather driving (I wouldn’t consider this essential for boston, but driving to outdoorsy things in the winter is less stressful with this feature). Also wanted decent highway mileage, mainly for environmental reasons. I ended up getting a 7-year-old Subaru Outback with just over 100k miles on it. It’s been a year now and I’m reasonably happy with the purchase.