I gotta admit, I'm finding myself becoming more and more willing to consider spending real money on a car, and maybe even a new one. For all my life, I've been "that guy". The guy who bought bombs for a few hundred dollars. Then spend hundreds of hours and dollars keeping them running. I'm getting to the point of seriously considering buying a car that doesn't need work, and won't need work for many years. That way I would have time to play with toys.
^^^This. I NEVER ever ever ever ever thought I'd have a new car. When Mamma got pregnant, I was still in the "Hmmm, this is a great opportunity to buy that old volvo wagon I've always wanted" mindset.
The turning point for me was this winter: It's freezing f*cking cold out, I load pregnant mamma into the 87 Civic and we head to work. 5 minutes up the road, the civic throws the alternator belt. No big deal, except I can't find another belt, AND the integra is axle-less, pulled apart waiting on new ones (I had planned on doing them that weekend.)
Pick up axles from the parts store, and long story short, it turns into a berkeleying project, and we don't make it into the shop that day.
At that point, I would've given up a nut to have a honda salesman pull in the driveway and say "Sign here, and pay 'x' per month for your new car."
I started looking at stuff in the ~$10k range...about $8k more than I had ever paid for a car. I had never even considered financing before. After driving a couple used $10k cars, I really just couldn't see paying that much money for something that was going to need maintenance soon, didn't have service records, etc.
Honda was advertising a lease for 2011 Fits for 0/0/0 and $190/month. We looked at the lease deal, and even though it was a great one (for a lease,) aside from the low payment, it didn't make much sense to me to lease rather than buy @ 0.9%.
I paid a couple grand more for a NEW honda fit than I would have for a used one with 60k miles, and I absolutely love the thing.
Bottom line: With a new baby and another birthday around the corner, I think I'm okay with saying "I'm getting too old for this E36 M3" i.e., stuff constantly breaking down. It's sooooo nice to have one car in the stable that I don't have to worry about.
I still feel like royalty every time I press the A/C button and the compressor kicks on.
OR:
Short answer to OP: When it's a 2-3 year old honda versus a new one.