my case, doing what Soy Celeste and The Lost do and come out net 0 or ahead is almost impossible since I put a ton of miles on my cars.

The only vehicle where a lease actually made sense for me would be my pickup truck. (It's a 2011 purchased new, and I've only put 42,000 miles on it so far). In the end, we decided to purchase instead of lease. Why? Because the truck will most likely last 20 years with minimal maintenance because of the miles I put on it, and with a lease I'd have to keep with the perpetual monthly payment.

The downside? I now have a really nice 2011 truck with 40k miles on it. If I was leasing, I'd have a new 2020 truck right now with 3,000 miles on it. I'd also still have a triple digit monthly payment.

It's all opportunity cost.

The annual preventive and breakdown maintenance on my old 2003 L322 range rover would be equivalent to about 2 to 3 months of lease payments on a standard SUV. Maybe 1.5 months of lease payments on an equivalent new Range Rover.

The downside to buying used, is primarily that you are in an older car/body style. Maintenance on modern rigs isn't really all that much under 200k, even for luxury "unreliable" cars.