Your perspective resonates with me! I have 3 kids under 6 years old, and I can definitely see this easily creeping up in my future.

My family situation is partly why I just went with plain old VMs and a Linux Distro with a 10 year support cycle. Its easy to keep all the moving parts in my head, and I figure I can mostly coast for 10 years and then reevaluate.

Thanks for reminding me, I also need to replace my UPS battery...