For looks - I like the old boats. For driving - the yellow one will do.
I love cars - and the old ones always fascinate me - as I look at them thinking what it must have been like driving them.
Where I draw the line is OWNING one - as you say maintenance is a bitch.
Many moons ago we had a Merc 190 (1960) model - not that old by a long stretch - but maintenance was expensive - and besides it was hell to drive. Like a blooming bus. That put me off owning old cars for life.
I love to photograph them though - and my preference is the (not so old) cars with wings.