Older prestige cars are great, but in my country (Uruguay) they are heavily taxed - you have to pay 2.5% of its calculated value in taxes to the local government, plus a very heavy insurance extra, and maintenance is pretty expensive as well.
Maybe in the US the bigger factor in maintenance is labor rather than parts, so the difference between a better and a cheaper car is not as much? And I understand that government doesn't punish displays of wealth with heavy taxes as much.
What, you have to pay extra on a used car? All countries require registration (which is a tax) but to my experience, it's calculated on engine size or other economy/pollution proxy.
In places like the USA, a 10 year old Merecedes is probably worth 10% of it's original purchase price, but if it has been treated well (and continues to be treated well), is probably only 50% through it's useful service life. The sweet spot is probably at about 6 years old and 60,000 miles, when most buyers would stop considering it as an option. Buying them at about that age and keeping for 5-7 years is my advice, if you know how to sort the pearls from the swine.
The big cost for keeping old prestige cars on the road is a combination of parts and labour, but labour is pretty much the same for all cars (assuming you stay away from the dealer). Finding used/cheap parts and/or doing some of the work yourself is the best way.
I don't ever want to live anywhere where 'displays of wealth' are punished. I'm not rich, but I have no beef with people who are.
Maybe in the US the bigger factor in maintenance is labor rather than parts, so the difference between a better and a cheaper car is not as much? And I understand that government doesn't punish displays of wealth with heavy taxes as much.