Yeah, given the miles I put on my vehicles in 20 years my wife's car would have 300k miles on it, my truck would have 500k miles on it... Given that my wife not mechanically inclined at all, I like to have her in a new car, I couldn't see having her running around in something with 100k miles on it that is 10 years old, her safety is way more important to me than milking a car till the wheels fall off... I look at vehicles from a different perspective than you do clearly...
Maintenance adds up and IF you have to pay someone to do it for you because you don't have the time, tools or facility to do the work it becomes very expensive quickly...
Paying cash for a car is one of the most short sighted financial decisions you could make... Whenever 0% financing is available on a car, tractor, etc smart money is to take it unless you're giving up dollars off the purchase price to do so..
I can see the forest just fine, I just choose to have my forest include all my financial / life decisions not just my car purchases... I like to eliminate my liability for a vehicle by entering into a lease that guarantees the amount of depreciation I will pay.. I prefer to buy things that appreciate or hold their value, cars just sink like a rock and are nothing but an expense... Now this all assumes that I can continue to get super cheap leases, it helps having an 750- 800 credit score and enough cash in the bank to pay the lease up front (not that I ever would pay a lease up front) If lease price climb and I can buy a 1-2 year old car with 12-20k miles on the clock for $50-60 a month more on a 72 month loan than I could lease the new equivalent for then I might be able to justify the liability of owning another car... I don't mind owning / borrowing money to 'buy' my truck because my employer basically covers my car payment and I am running around in 'my' truck on their dime so if I have to sink $500-$1000 a year in maintenance cost into it, it's easier to stomach...
Not sure why you'd think it's financially sound to not have full coverage on a $30,000 piece of gear that you're putting on public roads where you have almost no control over the fact that some drunk or distracted driver could cause an accident that would destroy the value you have in the vehicle?? Maybe you have a few million bucks in the bank and you're in a totally different league than I am..
Doubt there is much of a point of seeing who 'comes out ahead' because really, that is such a subjective thing, we're probably both coming out a head in our own needs / situation... If you like keeping cars for a very long time and you're able to work on 'em and make 'em last for a low cost then great for you, I just prefer to treat cars as use items and replace them frequently..