I do have to say one major flaw in owning older supercars and high end cars and that's that it can probably be a bit embarrassing when your 2007 Bentley doesn't have Bluetooth, USB or AUX which are standard in most Fiestas today.
I mean, that high end escort is going to be a bit miffed when she has no where to plug in her phone
Just one thing to consider. I wouldn't worry about it with a car like an Aston/Ferrari/Lambo...etc which you buy for it's appearance and stature, but Top Gear did an episode on exactly this issue. Buying an older high end car or a new cheap car. You miss out on a lot in older cars.