I was thinking this the other day, watching tv on our ancient Ferguson TX; which I can't figure out how old it is, but it must be somewhere between 20-30 years old and it is still working well enough that there is absolutely NO WAY I'm replacing it before it dies - it's outlived many more recent offerings, I'm sure. But without realising it, old has become the new new for me.
My cameras, being second hand film cameras, are all old. The oldest must be my Great Grandpa's No.2A Folding Autographic Brownie from 1926, the newest being the Canon Ixus L-1 from 1997. And then there's the rest everywhere in between. And they are all lovely. I wouldn't swop my Yashica Mat for a Nikon D300 (or whatever is good at the mo') because it's just not the same thing.
My computer is old by computer standards: 2003. Six years isn't bad going. Fingers crossed it keeps going longer. It's old technology as it's a PPC processor. Part of the enjoyment is/has been using sometime different. But with a new machine there's either x86 or x86. It will very soon be "obsolete" in that it won't be able to run the latest OS. But it won't be obsolete in that it will still do what I need it to do.
As technology progresses it seems to converge and refine whereas with old technology there's a lot more diversity. Which to me translates as more things to try out. And not all of it is past its sell by date. It still does the trick.
I'm not anti-new technology. Far from it, but being into new technology does come at a cost (Mind you, being into old technology can come at a cost as well, especially with some cameras!)
The only downside is being left behind. But you don't have to stay behind permanently, just lag a little.