Definitely when it comes to gaming. I probably have as much fun playing Street Fighter II with a usb-snes controller + emu as I do playing with the GearVR, mode

Definitely when it comes to gaming. I probably have as much fun playing Street Fighter II with a usb-snes controller + emu as I do playing with the GearVR, modern games, etc. As long as it isn't holding you back from productivity - there's no real downside to being held back by nostalgia. If keeping old tech is holding you back in any way (security flaws, being out of touch with your industry, unable to collaborate, etc.) - then you'll find the happiness quotient goes up if you upgrade ;)