I got a 986 Boxster 4 years ago as a project and whilst I've run it on a relative shoestring, I've still poured a fair bit of money into it.
However, it's been the best automotive investment I ever made and in terms of enjoyment, it's paid for itself already. Driving with the hood down through vineyards in Bordeaux last year and over Alpine passes this year are memories that I'll take to the grave.
I think that's how you have to see cherished/classic cars. The value is in the ownership and enjoyment – and for me, the satisfaction of tinkering and fixing things myself. Whatever you get back when it comes to sell is a bonus, and if selling for a knockdown price is too painful, then keep it if you can. And drive it.
I've now started my hunt for a "budget" GranTurismo (I was considering a QPV but have decided to wait and get what I really want). I do feel for owners whose coupes aren't holding their value and whilst it may improve my chances of bagging a bargain, it also speaks to future depreciation that I've already accepted as part of the package when I get one.
I don't wish to appear insensitive to owners who may need to liquidate an asset and are taking a major hit – this is just my opinion based on my recent limited experience of owning a car that's more than just a mode of transport.
Oh, and as for Antipodean prices, even a 986 Boxster is silly money there!