I want a spatially aware calendar. In my case it could probably use driving times alone but for people who were willing to fly, it could use flight times plus driving and wait times, and for that matter, ability to know what you're willing to spend on flights to know if flying is viable.
Then, given a set of things I'm invited to, hopefully location-tagged, figure out what's possible given the things I *have* accepted, or my default location, plus time that's available for travel (leave me things like time to sleep, and potentially work. bonus points: track pto, and allocate it as needed)
This is extreme, and I will never do it. The time of my life where I would do something like this is gone, I think. This probably means I'm on my way to being a manager. Bleh.