Ask HN: How to avoid being a digital pack rat?

I am finally admitting to myself that I am a digital hoarder. I just upgraded my laptop and realized how much stuff I drag along each time I upgrade. I have VMs from the last three laptops and two workstations that I keep lugging around. At this rate my next laptop will have to have a 1tb drive just for the old VMs. I tell myself that I will cleanup later but I am at a point where it will take a significant effort to consolidate and minimize.

How can I avoid this in the future? How do you streamline your file storage and application management?