I have no problem upgrading if there is newer technology I want, especially with eReaders and MP3 players. I upgraded to a Pearl screen and I will upgrade to lighted Kindle when they come out.
However on other technology such as my PC not until I have to which is getting pretty close. I bought my desktop in 2007 and I'm starting to have issues. Hard Drives dying less than a year old, Bad Disk block on my DVD Writer everytime I use it. I suspect the SATA controller on the motherboard may be going. So this means it's time to save up for a new PC.
I'd love a new phone but I am happy with little Android one I own. I just wish it played Hulu Plus.